Benzyl 3-aminopropanoate → HCID 19037102, compound

HRID 976486Notes

Reaction equation

HRID 976486 reaction equation
[C:1]([S:4][CH2:5]/[C:6](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)/[C:7]([OH:9])=O)(=[O:3])[CH3:2].[NH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>>[O:9]=[C:7]([NH:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])/[C:6](/[CH2:5][S:4][C:1](=[O:3])[CH3:2])=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 1116164Benzyl 3-aminopropanoateHCID 86750591HCID 86750591, compound

Product 1

HCID 19037102HCID 19037102, compoundYield 47%

Procedure

The (Z)-2-acetylthiomethyl-3-(4-trifluoromethylphenyl)propenoic acid obtained in step C is coupled with benzyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield=47% (purification by flash chromatography, eluent: ether/petroleum ether 6/4) m.p. 79° C. IR (nujol): 3280, 1740, 1690, 1640, 1620 cm-1 1H NMR (CDCl3 /TMS): 7.70 (s, 1H); 7.55 (AB, 2H, J=8 Hz); 7.45 to 7.20 (m, 7H); 6.95 (t, 1H, J=6 Hz); 5.15 (s, 2H); 3.90 (s, 2H); 3.40 (q app., 2H, J app.=6 Hz.); 2.65 (t, 2H, J=5 Hz); 2.30 (s, 3H). Microanalysis: C23H22O4NSF3Calc. % C=59.35 H=4.76 N=3.01 Found. % C=59.17 H=4.73 N=2.87

Workup

  1. customYield=47% (purification by flash chromatography, eluent: ether/petroleum ether 6/4) m.p. 79° C

Sources & evidence

ORD record
ord-54fbb144491e4824b8dfd03d6020ff8f
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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