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

HRID 976474Notes

Reaction equation

HRID 976474 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][CH3:23])=[O:21]>>[O:9]=[C:7]([NH:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[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 192794Methyl beta-alanateHCID 86750583(E)-2-acetylthiomethyl-3-phenylpropenoic acid

Product 1

HCID 86750584methyl N-(E)-[1-oxo-2-(acetylthiomethyl)-3-phenylpropenyl]-beta-alaninateYield 60%

Procedure

The (E)-2-acetylthiomethyl-3-phenylpropenoic acid described in Example 1 (step C) is coupled with methyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield: 60% (after flash chromatography, eluent: ether/petroleum ether 6/4) m.p. 54° C. IR (nujol): 3280, 1720, 1680, 1630, 1610 cm-1 1H NMR: 7.20, (s, 5H); 6.80 (s, 1H); 5.90 (broad s, 1H); 3.85 (s, 2H); 3.50 (s, 3H); 3.60 to 3.30 (m, 2H); 2.35 (t, 2H, J=5.30 Hz); 2.25 (s, 3H). Microanalysis: C16H19O4NS Calc. % C=59.79 H=5.96 N=4.36 Found. % C=59.67 H=6.28 N=4.47

Sources & evidence

ORD record
ord-ea84e5abd9aa40e5aa7a31e26a503378
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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