Supporting Information. Enzymatic Process for N-Substituted (3S)- and (3R)-3- Hydroxypyrrolidin-2-ones
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1 Supporting Information Enzymatic Process for N-Substituted (3S)- and (3R)-3- Hydroxypyrrolidin-2-ones Amarjit Singh*, James Falabella, Thomas L LaPorte, and Animesh Goswami Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States *Corresponding author. Tel.: ; Fax: amarjit.singh@bms.com. Table of contents 1. Figure S1: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at different water concentrations (a) Full data (b) data from 1-10 h 2. Figure S2: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at different temperatures 3. Figure S3: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a in the presence of different concentrations of acetic acid 4. Figure S4: Novozym 435 catalyzed resolution of 50 g batch of RS-acetate RS-4a 5. Figure S5: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a in the presence of different enzyme loading 6. Figure S6: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 20 g/l concentration 7. Figure S7: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 40 g/l concentration 8. Figure S8: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 60 g/l concentration Page 1 of 16
2 9. Figure S9: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 80 g/l concentration 10. Figure S10: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 100 g/l concentration 11. Figure S11: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 20 g/l, 40 g/l, 60 g/l, 80 g/l, and 100 g/l concentration with different water concentrations 12. Figure S12: Novozym 435 catalyzed hydrolysis of RS-propionate RS-4b and RSbutyrate RS-4c at 20 g/l concentration 13. Table S1: Enzymatic preparation of (S)-1-(2-fluoro-4-iodophenyl)-3-hydroxypyrrolidin- 2-one S Table S2: Optimization of Novozym 435 catalyzed hydrolysis of RS-hexanoate RS-4d Page 2 of 16
3 1. Figure S1: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a in different water concentrations. The reactions were run in a jacketed 125 ml glass reactor and the reaction temperature 25 C was maintained by using a water circulator. RSacetate RS-4a (1.0 g, Mw = , 3.19 mmol), acetonitrile (47.5 ml, anhydrous), and different percentages of water were added to the jacketed reactor and the reaction mixture was stirred at 25 C for 10 min. Novozym 435, (250 mg, w/w, enzyme-to-substrate ratio 1:4) was added to the reaction mixture with continuous stirring under the same reaction conditions. Samples (50 µl) were taken out, diluted with acetonitrile (950 µl), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown Page 3 of 16
4 in the figures S1a and S1b. The data in figure S1b was extracted from figure S1a and shows conversion from 0 h to 10 h at different water concentrations. 2. Figure S2: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at different temperatures. The reactions were done in 125 ml jacketed glass reactor and the reaction temperature was controlled using a water circulator. Racemic acetate RS-4a (1.0 g, Mw = , 3.19 mmol), acetonitrile (45 ml, 90%, anhydrous), and water (5 ml, 10%, mmol, 87 mol equiv to acetate RS-4a) were added to a reactor and the reaction mixture was stirred at predetermined temperature for 10 min. Novozym 435 (250 mg, w/w, enzyme-to-substrate ratio 1:4) was added to the reaction mixture with continuous stirring under same reaction conditions. Samples (50 µl) were taken out, diluted with acetonitrile (950 µl), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results from HPLC analysis at different temperatures are shown in Figure S2. Insert in figure S2 shows the conversion at 3 h and 7 h at different temperatures. Page 4 of 16
5 3. Figure S3: Novozym 435 catayzed hydrolysis of RS-acetate RS-4a in the presence of different concentrations of acetic acid. Acetic acid is the byproduct formed after enzymatic hydrolysis of RS-4a. Three experiments were run to study the effect of acetic acid. Racemic acetate RS-4a (1.0 g, Mw = , 3.19 mmol), acetonitrile (45 ml, anhydrous), and water (5 ml, 10%, mmol, 87 mol equiv to acetate RS-4a) were added to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. In the first reaction no acetic acid was added, in the second reaction, 0.5 mol equiv of acetic acid (Mw 60.05, d=1.049, 1.60 mmol, 91 µl) was added. In the third reaction, 1.0 mol equiv of acetic acid (Mw 60.05, d=1.049, 3.19 mmol, 183 µl) was added. The reactions were stirred for 5 min after the addition of acetic acid. To each reaction mixture, Novozym 435 (250 mg, w/w, enzyme-to-substrate ratio 1:4) was added with continuous stirring under the same reaction conditions. Samples (50 µl) were taken out, diluted with acetonitrile (950 µl), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results from the HPLC analysis are shown in Figure S3. Page 5 of 16
6 4. Figure S4: Novozym 435 catalyzed resolution of 50 g batch of RS-acetate RS-4a For figure S4, the experimental details are discussed in the experimental, and results and discussion sections of the manuscript. Page 6 of 16
7 5. Figure S5: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a catalyzed by different enzyme loading. Racemic acetate RS- 4a (1.0 g, Mw = , 3.19 mmol, 20 g/l), acetonitrile (49.5 ml, anhydrous), and water (500 µl, 1%, mmol, 8.7 mol equiv to acetate RS-4a) were added to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. Nine reactions were run using different concentrations of Novozym 435 with continuous stirring under similar reaction conditions as shown in the Figure S5. Samples (50 µl) were taken out, diluted with acetonitrile (950 µl), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown in the Figure S5. Page 7 of 16
8 6. Figure S6: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 20 g/l concentration Racemic acetate RS-4a (1.0 g, Mw = , 3.19 mmol, 20 g/l), acetonitrile (49.5 ml, anhydrous), and water (500 µl, 1%, mmol, 8.7 mol equiv to acetate RS-4a) were added to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. Novozym 435 (40 mg, w/w, enzyme-to-substrate ratio 1:25, enzyme loading 4%, concentration 0.8 g/l) was added to the reaction mixture with continuous stirring under same reaction conditions. Samples (50 µl) were taken out, diluted with acetonitrile (950 µl), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown in the Figure S6. Page 8 of 16
9 7. Figure S7: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 40 g/l concentration. Racemic acetate RS-4a (2.0 g, Mw = , 6.39 mmol, 40 g/l), acetonitrile (49.5 ml, anhydrous), and water (500 µl, 1%, mmol, 4.35 mol equiv to acetate RS-4a) were added to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. Novozym 435 (80 mg, w/w, enzyme-to-substrate ratio 1:25, enzyme loading 4%, concentration 1.6 g/l) was added with continuous stirring under same reaction conditions. Samples (25 µl) were taken out, diluted with acetonitrile (975 µl), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown in the Figure S7. The reaction was repeated under similar conditions except different ratio of acetonitrile (49.0 ml, anhydrous) and water (1.0 ml, 2%, mmol, 8.7 mol equiv to acetate RS-4a) were used, so that mol equiv of water to acetate RS-4a is consistent with 20 g/l concentration reaction. The results are shown in Figure S7. Page 9 of 16
10 8. Figure S8: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 60 g/l concentration. Racemic acetate RS-4a (3.0 g, Mw = , 9.58 mmol, 60 g/l), acetonitrile (49.5 ml, anhydrous), and water (500 µl, 1%, mmol, 2.9 mol equiv to acetate RS-4a) were added to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. Novozym 435 (120 mg, w/w, enzyme-to-substrate ratio 1:25, 4% loading and 2.4 g/l concentration) was added to the reaction mixture with continuous stirring under same reaction conditions. Samples (25 µl) were taken out, diluted with acetonitrile (1.475 ml), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown in the Figure S8. The reaction was repeated under similar reaction conditions except the percentage of acetonitrile and water were different as shown below. Racemic acetate RS-4a (3.0 g, Mw = , 9.58 mmol, 60 g/l), acetonitrile (48.5 ml, anhydrous), and water (1.5 ml, 3%, mmol, 8.7 mol equiv to acetate RS-4a) were added to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. Novozym 435 (120 mg, w/w, enzyme-to-substrate ratio 1:25, 4% loading, 2.4 g/l) was added to the reaction mixture with continuous stirring under same reaction conditions. Samples (25 µl) Page 10 of 16
11 were taken out, diluted with acetonitrile (1.475 ml), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown below in the Figure S8. 9. Figure S9: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 80 g/l concentration. Racemic acetate RS-4a (4.0 g, Mw = , mmol, 80 g/l), acetonitrile (49.5 ml, anhydrous), and water (500 µl, 1%, mmol, 2.18 mol equiv to acetate RS-4a) were added to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. Novozym 435 (160 mg, w/w, enzyme-to-substrate ratio1:25, enzyme loading 4%, concentration 3.2 g/l) was added to the reaction mixture with continuous stirring under same reaction conditions. Samples (25 µl) were taken out, diluted with acetonitrile (1.975 ml), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown in the Figure S9. Another experiment was run under similar conditions except the percentages of acetonitrile and water were different as described below. Racemic acetate RS-4a (4.0 g, Mw = , mmol, 80 g/l), acetonitrile (48.0 ml, anhydrous), and water (2.0 ml, 4%, mmol, 8.7 mol equiv to acetate RS-4a) were added Page 11 of 16
12 to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. Novozym 435 (160 mg, w/w, enzyme-to-substrate ratio 1:25, enzyme loading 4%, concentration 3.2 g/l) was added to the reaction mixture with continuous stirring under same reaction conditions. Samples (25 µl) were taken out, diluted with acetonitrile (1.975 ml), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown in Figure S Figure S10: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 100 g/l concentration. Racemic acetate RS-4a (5.0 g, Mw = , mmol, 100 g/l), acetonitrile (49.5 ml, anhydrous), and water (500 µl, 1%, mmol, 1.74 mol equiv to acetate RS-4a) were added to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. Novozym 435 (200 mg, w/w, enzyme-to-substrate ratio1:25, enzyme loading 4%, concentration 4.0 g/l) was added to the reaction mixture with continuous stirring under same reaction conditions. Samples (25 µl) were taken out, diluted with acetonitrile (2.475 ml), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown in the Figure S10. The experiment was Page 12 of 16
13 repeated under similar reaction conditions except different percentages of acetonitrile and water were used as shown below. Racemic acetate RS-4a (5.0 g, Mw = , mmol, 100 g/l), acetonitrile (47.5 ml, anhydrous), and water (2.5 ml, 5%, mmol, 8.7 mol equiv to acetate RS-4a) were added to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. Novozym 435 (200 mg, w/w, enzyme-to-substrate ratio1:25, enzyme loading 4%, concentration 4.0 g/l) was added to the reaction mixture with continuous stirring under same reaction conditions Samples (25 µl) were taken out, diluted with acetonitrile (2.475 ml), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown in the Figure S Figure S11: Novozym 435 catalyzed hydrolysis of RS-acetate RS-4a at 20 g/l, 40 g/l, 60 g/l, 80 g/l, and 100 g/l concentration with 8.7 mol equiv of water. The results in Figure S11 are extracted from Figure S6-S10. Page 13 of 16
14 12. Figure S12: Novozym 435 catalyzed hydrolysis of RS-propionate RS-4b and butyrate RS-4c. RS-1-(6-Bromo-2- methylpyridin-3-yl)-2- oxopyrrolidin-3-yl propionate RS-4b (1.0 g, 20 g/l), acetonitrile 49.5 ml, and water 500 µl, 1% were added to a jacketed 125 ml glass reactor and the reaction mixture was stirred at 25 C for 10 min. Novozym 435, 40 mg (enzyme-to-substrate ratio 1:25) was added to the reaction mixture with continuous stirring under same reaction conditions. Samples (100 µl) were taken out, diluted with acetonitrile (1.9 ml), vortexed, filtered and analyzed by HPLC (see HPLC methods section). The results are shown in the Figure S12. Novozym 435 catalyzed hydrolysis of (RS)-1-(6-bromo-2- methylpyridin-3-yl)-2-oxopyrrolidin-3-yl butyrate RS-4c (1.0 g, 20 g/l) was carried out under similar conditions and results are shown in the Figure S12. Page 14 of 16
15 Table S1: Enzymatic preparation of (S)-1-(2-fluoro-4-iodophenyl)-3-hydroxypyrrolidin-2-one (S-1) Description Batch 1 Batch 2 Batch 3 Batch 4 Batch 5 Racemic alcohol 5.0 g 75 g 75 g 67 g 79 g Lipase PS mg 3.75 g 3.75 g g g Succinic anhydride 1.25 g g g g g 2-Methyltetrahydrofuran 100 ml 1.5 L 1.5 L 1.34 L 1.58 L Reaction time 6 h 5.5 h 5.5 h 7.5 h 8.5 h Yield 34.8% 37.1% 38.8% 42.5% 40.6% AP , ee >99.9% 99.9% 99.8% >99.9%, 98.9% 99.9% Reactions were run at 4 C and temperature was maintained by using a circulator Page 15 of 16
16 13. Table S2: Optimization of Novozym 435 catalyzed hydrolysis of RS-hexanoate RS-4d Page 16 of 16
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