Benzyl 3-aminopropanoate → HCID 19037116, compound

HRID 976489Notes

Reaction equation

HRID 976489 reaction equation
[C:1]([S:4][CH2:5]/[C:6](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH3:20])=[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]([O:17][CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 1116164Benzyl 3-aminopropanoateHCID 19967361HCID 19967361, compound

Product 1

HCID 19037116HCID 19037116, compoundYield 66%

Procedure

The (Z)-2-acetylthiomethyl-3-(4-propoxyphenyl)propenoic acid obtained in step C is coupled with benzyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield=66% (purification by flash chromatography, eluent: ether/petroleum ether 65/35)-oil IR: 3280, 1740, 1690, 1645, 1620 cm-1 1H NMR (CDCl3 /TMS): 7.50 (s, 1H); 7.35 to 7.15 (m, 7H); 6.95 to 6.75 (m, 3H); 5.15 (s, 2H); 4.00 to 3.50 (m, 6H); 2.65 (t, 2H, J=6 Hz); 2.30 (s, 3H); 1.80 (m, 2H, J app.=8 Hz); 1.00 (t, 3H, J=8 Hz). Microanalysis: C25H29O5NS Calc. % C=65.91 H=6.42 N=3.07 Found. % C=65.80 H=6.38 N=2.91

Workup

  1. customYield=66% (purification by flash chromatography, eluent

Sources & evidence

ORD record
ord-4f246ab1b57341b393415dceab20308d
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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