Methyl beta-alanate → methyl N-(E)-[1-oxo-2-(pivaloylthiomethyl)-3-phenylpropenyl]-betaalaninate

HRID 976480Notes

Reaction equation

HRID 976480 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][CH3:26])=[O:24]>>[O:12]=[C:10]([NH:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[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 192794Methyl beta-alanateHCID 86750589(E)-2-pivaloylthiomethyl-3-phenylpropenoic acid

Product 1

HCID 86750590methyl N-(E)-[1-oxo-2-(pivaloylthiomethyl)-3-phenylpropenyl]-betaalaninateYield 69%

Procedure

The (E)-2-pivaloylthiomethyl-3-phenylpropenoic acid described in Example 8 (step B) is coupled with methyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield: 69% (after flash chromatography, eluent: ether/petroleum ether 55/45) oil IR: 3300, 1730, 1660, 1630 cm-1 1H NMR (CDCl3): 7.20 (s, 5H); 6.75 (s, 1H); 5.90 (broad t, 1H); 3.80 (s, 2H); 3.50 (s, 3H); 3.60 to 3.25 (m, 2H); 2.40 (t, 2H, J=6.5 Hz); 1.20 (s, 9H) Microanalysis: C19H25NO4S Calc. % C=62.79 H=6.93 N=3.85 Found. % C=63.20 H=7.10 N=3.92

Sources & evidence

ORD record
ord-b93edfb07dee42d08149e77821712a7c
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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