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

HRID 976481Notes

Reaction equation

HRID 976481 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][CH3:27])=[O:24]>>[O:12]=[C:10]([NH:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[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 419889Ethyl 3-aminopropanoateHCID 86750589(E)-2-pivaloylthiomethyl-3-phenylpropenoic acid

Product 1

HCID 19037118ethyl N-(E)-[1-oxo-2-(pivaloylthiomethyl)-3-phenylpropenyl]-beta-alaninateYield 73%

Procedure

The (E)-2-pivaloylthiomethyl-3-phenylpropenoic acid described in Example 8 (step B) is coupled with ethyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield: 73% (after flash chromatography, eluent: ether/petroleum ether 55/45)-oil IR: 3300, 1710, 1650, 1620 cm-1 1H NMR (CDCl3): 7.20 (s, 5H); 6.75 (s, 1H); 6.0 (broad t, 1H); 3.95 (q, 2H, J=7.5 Hz); 3.80 (s, 2H); 3.40 (q app., 2H, J. app=6.40 Hz); 2.35 (t, 2H, J=5.9 Hz); 1.30 to 0.95 (m, 12H). Microanalysis: C20H27NO4S Calc. % C=63.63 H=7.21 N=3.71 Found. % C=63.35 H=7.16 N=3.52

Sources & evidence

ORD record
ord-15b7eb8158154d44b4d6c439bcbaba79
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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