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

HRID 976475Notes

Reaction equation

HRID 976475 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][CH3:24])=[O:21]>>[O:9]=[C:7]([NH:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[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 419889Ethyl 3-aminopropanoateHCID 86750583(E)-2-acetylthiomethyl-3-phenylpropenoic acid

Product 1

HCID 19037101ethyl N-(E)-[1-oxo-2-(acetylthiomethyl)-3-phenylpropenyl]-beta-alaninateYield 68%

Procedure

The (E)-2-acetylthiomethyl-3-phenylpropenoic acid described in Example 1 (step C) is coupled with ethyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield=68% (chromatography on silica, eluent: ether/petroleum ether 6/4) m.p.<50° C. IR (nujol): 3300, 1730, 1690, 1640, 1610 cm-1 1H NMR: (CDCl3 /TMS)=7.20, (s, 5H); 6.75 (s, 1H); 6.00 (broad s, 1H); 3.95 (q, 2H, J=6, 7 Hz); 3.85 (s, 2H); 3.40 (q app., 2H, J app.=6.2 Hz); 2.30 (t, 2H, J=6.7 Hz); 2.30 (s, 3H); 1.15 (t, 3H, J=6.7 Hz). Microanalysis: C17H21O4NS Calc. % C=60.87 H=6.31 N=4.18 Found. % C=60.12 H=6.22 N=3.92

Sources & evidence

ORD record
ord-4c583a5214374ef780f29e201e26d3c3
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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