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1 Supplementary Information Synthesis and antioxidant evaluation of enantiomerically pure bis- (1,2,3-triazolylmethyl)amino esters from modified α-amino acids Juan I. Sarmiento-Sánchez a *, Adrián Ochoa-Teran b and Ignacio A. Rivero b * a Facultad de Ingeniería, Universidad Autónoma de Sinaloa, Blvd. de las Américas, S/N, Culiacán, Sinaloa, C.P , Mexico b Centro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Apdo. Postal 1166, 22500, Tijuana, B.C., Mexico * authors with equal contribution. Corresponding address: Facultad de Ingeniería, Universidad Autónoma de Sinaloa, Blvd. de las Américas, S/N, 80040, Culiacán, Sinaloa, México. Tel. +52 (667) address: jsarmiento@uas.edu.mx or irivero@tectijuana.mx S1
2 CONTENIDO GENERAL PROCEDURE FOR THE SYNTHESIS OF Α-HALOMETHYL KETONES... 3 GENERAL PROCEDURE FOR THE SYNTHESIS OF DI-PROPARGYL Α-AMINO ESTERS... 4 FIGURE S1 - (S)- METHYL 2- (DI(PROP- 2- YN- 1- YL)AMINO)PROPANOATE (11A)... 6 FIGURE S2 - ETHYL 2- (DI(PROP- 2- YN- 1- YL)AMINO)ACETATE (11B)... 7 FIGURE S3 - (S)- METHYL 2- (DI(PROP- 2- YN- 1- YL)AMINO)- 3- (1H- INDOL- 3- YL)PROPANOATE (11C) FIGURE S4 - (S)- METHYL 2- (DI(PROP- 2- YN- 1- YL)AMINO)- 3- PHENYLPROPANOATE (11D) FIGURE S5 - (S)- METHYL 2- (DI(PROP- 2- YN- 1- YL)AMINO)- 3- HYDROXYPROPANOATE (11E) FIGURE S6 - (S)- METHYL 2- (((1- ((R)- 3- (DIBENZYLAMINO)- 2- OXOBUTYL)- 1H- 1,2,3- TRIAZOL- 4- YL)METHYL)((1- ((S)- 3- (DIBENZYLAMINO)- 2- OXOBUTYL)- 1H- 1,2,3- TRIAZOL- 4- YL)METHYL)AMINO)PROPANOATE (6A) FIGURE S7 - (R)- METHYL 2- (((1- ((R)- 3- (DIBENZYLAMINO)- 2- OXOBUTYL)- 1H- 1,2,3- TRIAZOL- 4- YL)METHYL)((1- ((S)- 3- (DIBENZYLAMINO)- 2- OXOBUTYL)- 1H- 1,2,3- TRIAZOL- 4- YL)METHYL)AMINO)- 3- (1H- INDOL- 3- YL)PROPANOATE (6B) FIGURE S8 - ETHYL 2- (((1- ((R)- 3- (DIBENZYLAMINO)- 2- OXOBUTYL)- 1H- 1,2,3- TRIAZOL- 4- YL)METHYL)((1- ((S)- 3- (DIBENZYLAMINO)- 2- OXOBUTYL)- 1H- 1,2,3- TRIAZOL- 4- YL)METHYL)AMINO)ACETATE (6C) FIGURE S9 - (R)- METHYL 2- (((1- ((R)- 3- (DIBENZYLAMINO)- 2- OXOBUTYL)- 1H- 1,2,3- TRIAZOL- 4- YL)METHYL)((1- ((S)- 3- (DIBENZYLAMINO)- 2- OXOBUTYL)- 1H- 1,2,3- TRIAZOL- 4- YL)METHYL)AMINO)- 3- HYDROXY PROPANOATE (6D).. 16 S2
3 1 General procedure for the synthesis of α-halomethyl ketones In a round bottom flask equipped with an addition funnel was added α-dibenzylamino ester (1 equiv), chloroiodomethane or dibromomethane (2.5 equiv), 50 ml of anhydrous THF at -78 C under inert atmosphere (argon) with constant stirring. Next, a solution of methyllithium 1.5 M (2.5 equiv) was added dropwise and then allowed to react for 30 min at -78 C with constant stirring. A saturated solution of ammonium chloride (20 ml) was then added and kept with stirring until it reached room temperature. The product was extracted with diethyl ether (3 x 20 ml) and the extracts were combined and dried over anhydrous sodium sulfate. After evaporation of the solvent, the resulting oil was used for the next step. (S)-1-chloro-3-(dibenzylamino)-2-butanone (10a). For full characterization see (Barluenga et al., 1995), yield 86%; pale yellow oil; 1 H NMR (CDCl 3, 200 MHz): δ (m, 10H), 4.56 (d, 1H, J = 15.9 Hz), 4.20 (d, 1H, J = 15.9 Hz), 3.70 (d, 2H, J = 13.6 Hz), (m, 1H), 3.42 (d, 2H, J = 13.6 Hz), 1.22 (d, 3H, J = 6.6 Hz); 13 C NMR (CDCl 3, 50 MHz): δ 203.0, 138.4, 128.7, 128.6, 127.5, 61.0, 54.6, 47.8, chloro-3-(dibenzylamino)-2-propanone (10b). Yield 80%; pale yellow oil; 1 H NMR (CDCl 3, 200 MHz): δ (m, 10H), 4.14 (s, 2H), 3.66 (s, 4H), 3.34 (s, 2H); 13C NMR (CDCl3, 50 MHz): δ 201.8, 138.0, 129.8, 128.5, 127.5, 60.1, 59.1, (S)-1-chloro-3-(dibenzylamino)-4-phenyl-2-butanone (10c). For full characterization see ref.(barluenga et al., 1995), yield 90%; pale yellow oil; 1 H NMR(CDCl 3, 200 MHz): δ (m, 15H), 4.43 (d, 2H, J = 15.9 Hz), 3.82 (d, 2H, J = 12.7 Hz), 3.66 (dd, 1H, J = 3.7, 9.3 Hz), 3.55 (d, 2H, J = 13.5 Hz), (dd, 1H, J = 9.4, 13.3 Hz), (dd, 1H, J = 3.7, 13.2 Hz); (CDCl3, 50 MHz): δ 200.5, 138.6, 138.4, 129.4, 128.8, 128.6, 128.4, 127.5, 126.2, 66.6, 54.5, 47.8, S3
4 (S)-4-(tert-butildimethylsilyloxi)-1-chloro-3-(dibenzylamino)-2-butanone (10d). For full characterization see (Barluenga et al., 1999), yield 65%; pale yellow oil; 1 H NMR (CDCl 3, 200 MHz): δ (m, 10H), 4.74 (s, 2H), 4.35 (d, 2H, J = 14.3 Hz), 4.09 (d, 2H, J =13.9 Hz), (dd, 1H, J = 6.6 Hz), 0.85 (s, 9H), (s, 6H); (CDCl 3, 50 MHz): δ 201.7, 139.0, 128.9, 128.5, 127.3, 65.4, 64.9, 55.3, 48.3, 25.9, 18.1, -5.6, (S)-1-bromo-3-(dibenzylamino)-2-butanone (10e). For full characterization see ref. (Barluenga et al., 1999), yield 90%; pale yellow oil; 1 H NMR (DMSO, 200 MHz): δ (m, 10H), 4.27 (d, 1H, J = 13.2 Hz), 4.19 (d, 1H, J = 13.2 Hz), (m, 3H), 3.48 (d, 2H, J = 6.7 Hz), 1.27 (d, 3H, J = 6.7 Hz); 13 C NMR (DMSO, 50 MHz): δ 202.2, 138.8, 128.4, 128.0, 126.3, 60.9, 53.8, 35.1, bromo-3-(dibenzylamino)-2-propanone (10f). Yield 80%; pale brown oil; 1 H NMR (CDCl 3, 200 MHz): δ (m, 10H), 3.89 (s, 2H), 3.67 (s, 4H), 3.39 (s, 2H); 13 C NMR (CDCl 3, 50 MHz): δ 201.6, 138.0, 129.0, 128.5, 127.5, 60.7, 59.0, General procedure for the synthesis of di-propargyl α-amino esters In a round bottom flask was added α-amino ester hydrochloride (1 equiv), potassium iodide (0.5 equiv), sodium bicarbonate (2.5 equiv) and propargyl chloride (2.5 equiv) in 50 ml of THF/DMSO (4:1 v/v) and refluxed for 8 h with constant stirring. The reaction mixture was transferred to a separating funnel, added water (250 ml) and extracted with DCM (3 x 60 ml). The extracts were combined and dried over anhydrous sodium sulfate. After evaporation of the solvent, the resulting oil was purified by flash chromatography. (S)-methyl 2-(di(prop-2-yn-1-yl)amino)propanoate (11a). Yield 85%; yellow oil; R f 0.40 (ethyl acetate/petroleum ether 2:8 v/v); 1 H NMR (CDCl 3, 200 MHz): δ 3.72 (s, 3H), (m, 1H), 3.60 (d, 4H, J = 2.5 Hz), 2.26 (t, 2H, J = 2.3 Hz), 1.38 (d, 3H, J = 6.9 Hz). 13 C NMR (CDCl 3, 50 MHz): δ 173.5, 78.9, 73.1, 58.9, 51.7, 39.7, 15.8; IR (film): 3290, 2120, 2106, 1732, 1436 cm -1 ; ESI-MS m/z: 218 [M+K] + S4
5 Ethyl 2-[di(prop-2-yn-1-yl)amino]acetate (11b). Yield 67%, yellow oil, R f 0.36 (ethyl acetate/petroleum ether 2:8 v/v); 1 H NMR (CDCl 3, 200 MHz): δ (q, 2H, J = 6.9 Hz), 3.57 (d, 4H, J = 2.2 Hz), 3.45 (s, 2H), (t, 2H, J = 2.3 Hz), (t, 3H, J = 7.1 Hz); 13 C NMR (CDCl 3, 50 MHz): δ 170.2, 78.2, 73.7, 60.8, 53.5, 42.6, 14.2; FT-IR (film): 3290, 2120, 2106, 1744, 1444 cm -1 ; ESI-MS m/z: 218 [M+K] + Methyl (S)-2-[di(prop-2-yn-1-yl)amino]-3-(1H-indol-3-yl)propanoate (11c). Yield 87%; brown solid; m.p C; R f 0.38 (ethyl acetate/petroleum ether 1:1 v/v); 1 H NMR (CDCl 3, 200 MHz): δ 8.12 (s, 1H), (m, 1H), (m, 4H), (dd, 1H, J = 5.9 Hz), 3.72 (d, 4H, J = 2.2 Hz), 3.53 (s, 3H), (m, 2H), 2.27 (t, 2H, J = 2.2 Hz); 13 C NMR (CDCl 3, 50 MHz): δ 172.4, 136.1, 127.4, 122.8, 121.9, 119.4, 118.6, 111.2, 111.1, 79.3, 73.0, 64.6, 51.3, 39.9, 25.9; FT-IR (film): 3412, 3290, 2120, 2106, 1729, 1620, 1595, 1340, 1213, 1170 cm -1 ; ESI-MS m/z: 318 [M+Na] +, 333 [M+K] + Methyl (S)-2-[di(prop-2-yn-1-yl)amino]-3-phenylpropanoate (11d). Yield 74%; pale yellow oil; R f 0.80 (ethyl acetate/petroleum ether 1:1 v/v); 1 H NMR (CDCl 3, 200 MHz): δ (m, 5 H), (t, 1H, J = 7.7 Hz), 3.67 (d, 4H, J = 2.2 Hz), 3.57 (s, 3 H), 3.04 (d, 2H, J = 7.7 Hz), (t, 2H, J = 2.3 Hz); 13 C NMR (CDCl 3, 50 MHz): δ 171.9, 137.3, 129.2, 129.4, 126.6, 79.1, 73.0, 65.7, 51.3, 39.9, 36.29; FT-IR (film): 3290, 2120, 2108, 1730, 1604, 1168 cm -1 ; ESI-MS m/z: 256 [M+H] +, 278 [M+Na] + Methyl (S)-2-[di(prop-2-yn-1-yl)amino]-3-hydroxypropanoate (11e). Yield 59%; pale yellow oil; R f 0.85 (ethyl acetate/petroleum ether 1:1 v/v); 1 H NMR (CDCl 3, 200 MHz): δ (q, 2H, J = 7.1 Hz), (m, 2H), (t, 4H, J = 2.2 Hz), (m, 1H), (t, 2H, J = 2.3 Hz), (t, 3H, J = 7.1 Hz); 13 C NMR (CDCl 3, 50 MHz): δ 170.6, 79.3, 73.2, 64.1, 60.9, 59.8, 40.1, IR (film): 3416, 3290, 2120, 2108, 1730, 1188 cm -1 ; ESI-MS m/z: 210 [M+H] +, 232 [M+Na] +, 441 [2M+Na] + S5
6 Figure S1 - (S)-methyl 2-(di(prop-2-yn-1-yl)amino)propanoate (11a) S6
7 Figure S2 - Ethyl 2-(di(prop-2-yn-1-yl)amino)acetate (11b) S7
8 Figure S3 - (S)-methyl 2-(di(prop-2-yn-1-yl)amino)-3-(1H-indol-3-yl)propanoate (11c) S8
9 Figure S4 - (S)-methyl 2-(di(prop-2-yn-1-yl)amino)-3-phenylpropanoate (11d) S9
10 Figure S5 - (S)-methyl 2-(di(prop-2-yn-1-yl)amino)-3-hydroxypropanoate (11e) S10
11 Figure S6 - (S)-methyl 2-(((1-((R)-3-(dibenzylamino)-2-oxobutyl)-1H-1,2,3-triazol-4-yl)methyl)((1-((S)-3- (dibenzylamino)-2-oxobutyl)-1h-1,2,3-triazol-4-yl)methyl)amino)propanoate (6a) S11
12 HRMS-ESI Mass Spectrum SmartFormula Report Analysis Info Acquisition Date 5/10/2014 2:08:57 PM Analysis Name D:\Data\Entrenamiento\Data\Juansarmiento\EXP171_MSPositivo_2.d Method tune_low_lc_modificado.m Operator CBS_UAM_I Sample Name Instrument microtof Comment Acquisition Parameter Source Type ESI Ion Polarity Positive Set Nebulizer 5.0 Bar Focus Active Set Dry Heater 190 C Scan Begin 50 m/z Set Capillary 4500 V Set Dry Gas 2.0 l/min Scan End 2000 m/z Set End Plate Offset -500 V Set Divert Valve Source Meas. m/z # Ion Formula m/z err [ppm] msigma # Sigma Score rdb e Conf N-Rule C46H54N9O even ok Bruker Compass DataAnalysis 4.1 printed: 5/16/2014 1:44:34 PM by: CBS_UAM_I 1 of 1 S12
13 Figure S7 - (R)-methyl 2-(((1-((R)-3-(dibenzylamino)-2-oxobutyl)-1H-1,2,3-triazol-4-yl)methyl)((1-((S)-3- (dibenzylamino)-2-oxobutyl)-1h-1,2,3-triazol-4-yl)methyl)amino)-3-(1h-indol-3-yl)propanoate (6b) S13
14 HRMS-ESI Mass Spectrum SmartFormula Report Analysis Info Acquisition Date 5/10/2014 1:53:42 PM Analysis Name D:\Data\Entrenamiento\Data\Juansarmiento\EXP179_2MSPositivo_3.d Method tune_low_lc_modificado.m Operator CBS_UAM_I Sample Name Instrument microtof Comment Acquisition Parameter Source Type ESI Ion Polarity Positive Set Nebulizer 0.3 Bar Focus Active Set Dry Heater 190 C Scan Begin 50 m/z Set Capillary 4500 V Set Dry Gas 3.0 l/min Scan End 2000 m/z Set End Plate Offset -500 V Set Divert Valve Source Meas. m/z # Ion Formula m/z err [ppm] msigma # Sigma Score rdb e Conf N-Rule C54H59N10O even ok Bruker Compass DataAnalysis 4.1 printed: 5/16/2014 1:41:05 PM by: CBS_UAM_I 1 of 1 S14
15 Figure S8 - ethyl 2-(((1-((R)-3-(dibenzylamino)-2-oxobutyl)-1H-1,2,3-triazol-4-yl)methyl)((1-((S)-3- (dibenzylamino)-2-oxobutyl)-1h-1,2,3-triazol-4-yl)methyl)amino)acetate (6c) S15
16 Figure S9 - (R)-methyl 2-(((1-((R)-3-(dibenzylamino)-2-oxobutyl)-1H-1,2,3-triazol-4-yl)methyl)((1-((S)-3- (dibenzylamino)-2-oxobutyl)-1h-1,2,3-triazol-4-yl)methyl)amino)-3-hydroxy propanoate (6d) S16
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