Benzyl 3-aminopropanoate → HCID 15287118, compound

HRID 976491Notes

Reaction equation

HRID 976491 reaction equation
[C:1]([S:4][CH2:5]/[C:6](=[CH:10]\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)/[C:7]([OH:9])=O)(=[O:3])[CH3:2].[NH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>>[O:9]=[C:7]([NH:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])/[C:6](/[CH2:5][S:4][C:1](=[O:3])[CH3:2])=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 1116164Benzyl 3-aminopropanoateHCID 15340011HCID 15340011, compound

Product 1

HCID 15287118HCID 15287118, compoundYield 78%

Procedure

The (Z)-2-acetylthiomethyl-3-phenylpropenoic acid described in Example 1 (step B) is coupled with benzyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield: 78% (after recrystallization in ether) m.p. 80° C. IR: 3380, 1720, 1670, 1630, 1600 cm-1 1H NMR (CDCl3): 7.60 (s, 1H); 7.45 to 7.15 (m, 10H); 6.90 (broad t, 1H; 5.15 (s, 2H); 3.95 (s, 2H); 3.65 (q. app., J:6.1 Hz); 2.65 (t, 2H, J=6.1 Hz); 2.35 (s, 3H). Microanalysis: C22H23NO4S Calc. % C=60.48 H=5.83 N=3.52 Found. % C=66.29 H=5.78 N=3.51

Workup

  1. customYield: 78% (after recrystallization in ether) m.p. 80° C

Sources & evidence

ORD record
ord-0aee083cbb524c2896154dc1cb0c1206
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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