Benzyl 3-aminopropanoate → benzyl N-(E)-[1-oxo-2-(pivaloylthiomethyl)-3-phenylpropenyl]-beta-alaninate

HRID 976479Notes

Reaction equation

HRID 976479 reaction equation
[C:1]([S:7][CH2:8]/[C:9](=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)/[C:10]([OH:12])=O)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>>[O:12]=[C:10]([NH:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])/[C:9](/[CH2:8][S:7][C:1](=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5])=[CH:13]\[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 1116164Benzyl 3-aminopropanoateHCID 86750589(E)-2-pivaloylthiomethyl-3-phenylpropenoic acid

Product 1

HCID 86750588benzyl N-(E)-[1-oxo-2-(pivaloylthiomethyl)-3-phenylpropenyl]-beta-alaninateYield 63%

Procedure

The (E)-2-pivaloylthiomethyl-3-phenylpropenoic acid above is coupled with benzyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield: 63% (after flash chromatography, eluent: ether/petroleum ether 55/45) oil IR: 3320, 1725, 1650, 1620 cm-1 1H NMR (CDCl3): 7.30 (s, 5H); 7.20 (s, 5H); 6.75 (s, 1H); 4.90 (s, 2H); 3.80 (s, 2H); 3.45 (q app; 2H, J=6.0 Hz); 2.40 (t, 2H, J=6.5 Hz); 1.20 (s, 9H). Microanalysis: C25H29NO4S Calc. % C=68.31 H=6.65 N=3.19 Found. % C=68.02 H=6.73 N=3.01

Sources & evidence

ORD record
ord-f3be97a880f1487dadd43614edb2d687
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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