Benzyl 3-aminopropanoate → benzyl N-(Z)-[1-oxo-2-(acetylthiomethyl)-3-(4-methoxyphenyl)propenyl]-beta-alaninate

HRID 976483Notes

Reaction equation

HRID 976483 reaction equation
[C:1]([S:4][CH2:5]/[C:6](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)/[C:7]([OH:9])=O)(=[O:3])[CH3:2].[NH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>>[O:9]=[C:7]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])/[C:6](/[CH2:5][S:4][C:1](=[O:3])[CH3:2])=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 1116164Benzyl 3-aminopropanoateHCID 15287116(Z)-2-acetylthiomethyl-3-(4-methoxyphenyl)propenoic acid

Product 1

HCID 15287117benzyl N-(Z)-[1-oxo-2-(acetylthiomethyl)-3-(4-methoxyphenyl)propenyl]-beta-alaninateYield 74%

Procedure

The (Z)-2-acetylthiomethyl-3-(4-methoxyphenyl)propenoic acid obtained in step C is coupled with benzyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield: 74% (crystallization in a dichloromethane/petroleum ether mixture) m.p. 96° C. IR (nujol): 3280, 1740, 1690, 1640, 1620 cm-1 1H NMR (CDCl3 /TMS): 7.65 (s, 1H): 7.35 to 7.15 (m, 7H); 6.95 to 6.80 (m, 3H); 5.10 (s, 2H); 4.00 (s, 2H); 3.75 (s, 3H); 3.60 (q, 2H, J app.=6 Hz); 2.60 (t, 2H, J=6 Hz); 2.30 (s, 3H). 13C NMR (CDCl3): 196.2; 172.0; 167.1; 159.8; 137.9; 135.6; 130.9; 128.5; 128.2; 128.1; 127.2; 114.1; 66.3; 55.2; 35.6; 33.8; 30.2; 26.6. Microanalysis: C23H25O5NS Calc. % C=64.61 H=5.89 N=3.27 Found. % C=64.20 H=5.73 N=3.48

Workup

  1. customYield: 74% (crystallization in a dichloromethane/petroleum ether mixture) m.p. 96° C

Sources & evidence

ORD record
ord-ad781310845a4ec99186481a0f24d04d
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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