Supporting Information. Scale-up synthesis of tesirine
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1 Supporting Information Scale-up synthesis of tesirine Arnaud C. Tiberghien *, Christina von Bulow, Conor Barry, Huajun Ge, Christian Noti, Florence Collet Leiris #, Marc McCormick, Philip W. Howard, Jeremy S. Parker Spirogen, QMB Innovation Centre, 42 New Road, E1 2AX London, U.K. Pharmaron, No.6, Taihe Road, BDA,Beijing, , P.R.China Lonza AG, Rottenstrasse 6, CH Visp, Switzerland # Novasep Ltd, 1 Rue Démocrite, Le Mans, France Early Chemical Development, Pharmaceutical Sciences, IMED Biotech Unit, AstraZeneca, Macclesfield, UK. 1
2 Content 1) Thin-layer chromatography of 41 (normal phase) 2) GC and HPLC methods for all intermediates and tesirine 3) TBAF titration methods 4) DoE study on the TBS deprotection of 39 2
3 Figure S1: TLC of Pd(0) deprotection of 40 to 41. (15% MeOH in DCM, CAM stain) I-30 I-30/IPC IPC 40 (R f = 0.70) Macrocycle of 41 (R f = 0.73) 41 (R f = 0.40) Note: Macrocyclic form (top spot, streaking down). Ring-opened form (bottom spot) 3
4 Analytical method used from Vanillin to Tips acid 6 Diluent Injection volume XDB C18 (4.6*150 mm, 5 µm) 0.05% TFA in Water 0.05% TFA in Acetonitrile ACN 1.5 ml/min 5 μl temperature nm 11.1 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
5 Analytical method used from proline to Z-TBS-proline 13 Diluent Injection volume SB-PHENYL (4.6*150 mm, 3.5 µm) 0.05% TFA in Water 0.05% TFA in Acetonitrile ACN 1.0 ml/min 5 μl temperature nm 11.1 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
6 GC method used for NH-prolinol-TBS 14 DB-5, 30m*0.25mm, 1.0 µm Inlet Temp 250 Temp 300 Split Flow 10:1 Flow Mode Total Flow Oven Program H2 Flow Air Flow Make Up Flow Diluent 3.0 ml/min Flow 36.0 ml/min 40 hold for 3 min, Ramp 30 /min to 300, hold for 5 min ml/min ml/min 30.0 ml/min MeOH 6
7 Analytical method used from 15 to 29 Diluent Injection volume temperature Post time Symmetry C8, 4.6*100 mm, 3.5 um column Water ACN ACN 1.0 ml/min 5 μl 30 C 223 nm 30.0 minutes 3 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
8 Analytical method used from L-Valine to 24 Diluent 1 Diluent 2 temperature Post time Agilent, SB-Phenyl (4.6*150mm, 3.5 um) 0.05% TFA in Water 0.05% TFA in ACN Water ACN 1.0 ml/min 30 C CAD and 210 nm 15.1 minutes 4 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
9 Analytical method used for compound 38 Pre-column Xselect CSH C18, 2.5 μm, 150 mm x 4.6 mm Xselect CSH C μm, 3.9 mm x 5 mm Water Acetonitrile Diluent Acetonitrile / water 80 / 20 Injection volume temperature 1.0 ml/min 10 μl 50 C 223 nm 35 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
10 Analytical method used for compound 32 Pre-column Xselect CSH C18, 2.5 μm, 150 mm x 4.6 mm Xselect CSH C μm, 3.9 mm x 5 mm Water Acetonitrile Diluent Acetonitrile / water 80 / 20 Injection volume temperature 1.0 ml/min 10 μl 50 C 250 nm 35 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
11 Analytical method used for compound 33 Pre-column Xselect CSH C18, 2.5 μm, 150 mm x 4.6 mm Xselect CSH C μm, 3.9 mm x 5 mm Water % acetic acid Acetonitrile % acetic acid Diluent Acetonitrile / water 80 / 20 Injection volume temperature 1.0 ml/min 10 μl 50 C 250 nm 40 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
12 Analytical method used for compound 34 Pre-column Xselect CSH C18, 2.5 μm, 150 mm x 4.6 mm Xselect CSH C μm, 3.9 mm x 5 mm Water % acetic acid Acetonitrile % acetic acid Diluent Acetonitrile / water 80 / 20 Injection volume temperature 1.0 ml/min 10 μl 50 C 250 nm 48 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
13 Analytical method used for compound 39 Pre-column Xselect CSH C18, 2.5 μm, 150 mm x 4.6 mm Xselect CSH C μm, 3.9 mm x 5 mm Water Acetonitrile Diluent Acetonitrile / water 80 / 20 Injection volume temperature 1.0 ml/min 10 μl 50 C 223 nm 40 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
14 Analytical method used for compound 40 Pre-column Xselect CSH C18, 2.5 μm, 150 mm x 4.6 mm Xselect CSH C μm, 3.9 mm x 5 mm Water % acetic acid Acetonitrile % acetic acid Diluent Acetonitrile / water 80 / 20 Injection volume temperature 1.0 ml/min 10 μl 50 C 223 nm 35 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
15 Analytical method used for compound 41 Pre-column Xselect CSH C18, 2.5 μm, 150 mm x 4.6 mm Xselect CSH C μm, 3.9 mm x 5 mm Water % acetic acid Acetonitrile % acetic acid Diluent Acetonitrile / water 80 / 20 Injection volume temperature 1.0 ml/min 10 μl 50 C 223 nm 40 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
16 Analytical method used for tesirine Pre-column Diluent Injection volume temperature Acquity UPLC CSH C18, 1.7 μm, 150 mm x 2.1 mm Acquity UPLC CSH C18, 1.7 μm, 5 mm x 2.1 mm Water % acetic acid Acetonitrile % acetic acid Acetonitrile/water 50/ % acetic acid 0.5 ml/min 6 μl 50 C 223 nm 30 minutes Gradient Table Time (min) % Mobile Phase A % Mobile Phase B
17 Chiral analytical method used for L-alanine and L-valine Diluent Astec CHIROBIOTIC T ( mm, 5.0µm) Water Water 1.0 ml/min Injection Volume 5.0 µl temperature 30C CAD 15 minutes Isocratic flow % Mobile Phase A: %Mobile Phase B = 20:80 CAD Parameters Full scale range Filter 100 pa None %baseline offset 0 Sample interval Temp Set point 2/sec 30C 17
18 Chiral analytical method used for 21 Diluent CHIRALPAK IC (4.6*250mm, 5.0µm) 0.1% TFA in hexane 1.0 ml/min Injection Volume 10.0 µl temperature 30C 210 nm 20 minutes Isocratic flow % Mobile Phase A: %Mobile Phase B = 95:5 18
19 Chiral analytical method used for 22 Diluent CHIRALPAK IC (4.6*250mm, 5.0µm) 0.1% TFA in hexane 1.0 ml/min Injection Volume 5.0 µl temperature 30C 210 nm 35 minutes Isocratic flow % Mobile Phase A: %Mobile Phase B = 92:8 19
20 Chiral analytical method used for 23 Diluent CHIRALPAK IA-3 (4.6*50mm, 3.0µm) 0.1% TFA in hexane Isopropanol 1.0 ml/min Injection Volume 10.0 µl temperature 30C 220 nm 15 minutes Isocratic flow % Mobile Phase A: %Mobile Phase B = 90:10 20
21 Chiral analytical method used for 24 temperature Injection Volume Diluent Isocratic flow CHIRALPAK IC (4.6*250mm, 5.0µm) n-hexane 35C DAD (245 nm) 1.2 ml/min 5 ul 20 min % Mobile Phase A : %Mobile Phase B=60:40 21
22 Chiral analytical method used for 9 and 10 temperature Injection Volume Diluent Isocratic flow CHIRALPAK IC (4.6*250mm, 5.0µm) 0.1% TFA in n-hexane 0.1% TFA in 30C DAD (210 nm) 1.0 ml/min 5 ul 15 min % Mobile Phase A: %Mobile Phase B=80:20 22
23 Chiral analytical method used for 11 temperature Injection Volume Diluent Isocratic flow CHIRALPAK IC (4.6*250mm, 5.0µm) 0.1% TFA in n-hexane 0.1% TFA in 30C DAD (210 nm) 1.0 ml/min 5 ul 20 min % Mobile Phase A: %Mobile Phase B=80:20 23
24 Chiral analytical method used for 12 temperature Injection Volume Diluent Isocratic flow CHIRALPAK IA (4.6*250mm, 5.0µm) 0.1% TFA in n-hexane 0.1% TFA in 30C DAD (210 nm) 1.0 ml/min 5 ul 30 min % Mobile Phase A: %Mobile Phase B=90:10 24
25 Chiral analytical method used for 13 temperature Injection Volume Diluent Isocratic flow CHIRALPAK IC (4.6*250mm, 5.0µm) Hexane 30C DAD (210 nm) 1.0 ml/min 5 ul 40 min % Mobile Phase A: %Mobile Phase B=97:3 25
26 Chiral analytical method used for 15 temperature Injection Volume Diluent Isocratic flow CHIRALPAK IC (4.6*250mm, 5.0µm) Hexane 30C DAD (210 nm) 1.0 ml/min 5 ul 25 min % Mobile Phase A: %Mobile Phase B=85:15 26
27 Chiral analytical method used for 16 temperature Injection Volume Diluent Isocratic flow CHIRALPAK IC (4.6*250mm, 5.0µm) Hexane 30C DAD (210 nm) 1.0 ml/min 5 ul 20 min % Mobile Phase A: %Mobile Phase B=90:10 27
28 Chiral analytical method used for 18 temperature Injection Volume Diluent Isocratic flow CHIRALPAK IA-3 (4.6*250mm, 5.0µm) n-heptane 30C DAD (210 nm) 1.0 ml/min 5 ul 15 min % Mobile Phase A: %Mobile Phase B=95:5 28
29 TBAF titration method: Reagents and Devices: - Glacial Acetic acid M HClO4 in glacial acetic acid, standardized ml Calibrated glass syringe - Automatic titroprocessor with Solvotrode TM Procedure: With a calibrated glass syringe, inject 1.5 ml of the sample solution to be analysed into a 150 ml beaker with 80 ml glacial acetic acid (covered with watchglass). Titrate potentiometrically with 0.1 M HClO4 Calculation: Molarity = V(HClO4) x C(HClO4) x T(HClO4) / V(sample) V(HClO4) = Volume HClO4 in ml C(HClO4) = 0.1 (mol / L) T(HClO4) = Titer HClO4 V(sample) = 1.5 ml TBAF titration by Ion Chromatography: The column used for fluoride quantification was a IonPac AS16 analytical, 250 x 4 mm. Water was used as eluent (flow rate 1mL/min). The detection was done by conductivity. 29
30 DOE study on the TBAF/AcOH TBS deprotection During this study, the batch of TBAF used was titrated at 0.67M. All values stated reflects the true titre of the TBAF used. A racemization of the product can occur in the presence of an excess of TBAF reagent during the TBS deprotection step. A DOE (Design of Experiment) study was thus conducted to evaluate the impact of the most important parameters on conversion rate and diastereoisomer content. The aim was to improve the conditions to decrease the diastereoisomer level and ensure process robustness. 1) Presentation of the study The TBS deprotection step was run using a DOE plan with JMP software (version 12). Based on previous work, two main parameters were identified. The study on only two parameters allowed a full screening design. The values of these parameters are presented in the following table, based on experiments previously run: Parameter Level 1 Level 2 TBAF (number equivalents/tbs*) Ratio TBAF / AcOH *2 TBS groups to be deprotected on eq excess TBS on 38 All other parameters were fixed. The following experiments were planned: 2) Results 30
31 - Conversion results The following conversions were obtained: - Diastereoisomer content Note: As no analytical method was available to determine the proportion of the diastereoisomer on 40, the synthesis had to be continued up to SG3249. The analysis of crude SG3249 samples was sufficient to evaluate an estimated amount of diastereoisomer content. This content is reported based on the UPLC areas, compared to the SG3249 content (at RRT 0.99). The following results were obtained (including experiment 7 with excess TBAF): 31
32 3) DOE interpretation Based on conversion and diastereoisomer results, the following DOE interpretation could be made using the JMP software. - Diastereoisomer content The following results were obtained regarding the diastereoisomer content: The model was not found linear (with exclusion of central points from the interpretation). Overall, the TBAF/AcOH ratio was found the most important parameter influencing the diastereoisomer content. The model was found stable in the defined range (for a ratio TBAF/AcOH between 0.5 and 0.7). The impact of the number of equivalents of TBAF per TBS to be deprotected appeared less significant. 32
33 - Conversion (24 hours reaction) The following results were obtained regarding conversion rates (24 hours reaction): Comments: The model was found linear (with exclusion of central points from the interpretation). Overall, the number of equivalents of TBAF (per TBS to be deprotected) appeared as the most important parameter on the conversion. This interpretation is consistent with additional experiments where the reaction kinetics were improved while increasing the amount of TBAF (and keeping a fixed TBAF/AcOH ratio). The kinetics were also improved with further addition of TBAF at a fixed TBAF/AcOH ratio. As expected, the best conversions were obtained for higher amounts of TBAF and higher ratio of TBAF/AcOH. As a conclusion, a low diastereoisomer content was obtained in the defined range (1.2 eq 1.6 eq TBAF and ratio TBAF / AcOH ). The conversion rate can be improved using a higher amount of TBAF. 33
34 4) Model verification The model was checked using 1.54 equivalents of TBAF (per TBS) and a ratio TBAF/AcOH of 0.6. After TBS deprotection, chromatography purification of 40, synthesis of 41 and SG3249, the following results were obtained: Prediction Results obtained Conversion 24h 89.5% 86% Diastereoisomer content 0.70% 0.63% The results were found in agreement with the predicted model. 5) Conclusion The DOE study on the TBS deprotection step showed that the kinetics could be improved with a higher amount of TBAF (and while increasing the ratio TBAF / AcOH). However, the control of the ratio TBAF/AcOH between is required to ensure a low diastereoisomer content (below 1 A%) in SG3249. The prediction of the model was confirmed with the verification experiment (using 1.54 equivalents of TBAF and a ratio TBAF/AcOH of 0.6). Corrective actions, such as addition of extra TBAF (while keeping the same ratio TBAF/AcOH) and longer reaction time (up to 3 days), can also be implemented without any risk of degradation of the reaction mixture and impact on diastereoisomer content. 34
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