Benzyl 3-aminopropanoate → HCID 19037106, compound

HRID 976488Notes

Reaction equation

HRID 976488 reaction equation
[C:1]([S:4][CH2:5]/[C:6](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)/[C:7]([OH:9])=O)(=[O:3])[CH3:2].[NH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>>[O:9]=[C:7]([NH:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])/[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]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 1116164Benzyl 3-aminopropanoateHCID 86750592HCID 86750592, compound

Product 1

HCID 19037106HCID 19037106, compoundYield 56%

Procedure

The (Z)-2-acetylthiomethyl-3-(4-phenylphenyl) propenoic acid obtained in step C is coupled with benzyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield: 56% (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): 7.75 (s, 1H); 7.65 to 7.20 (m, 14H); 7.05 (t, 1H, J=5 Hz); 5.0 (s, 2H); 4.15 (s, 2H); 3.65 (q. app., 2H, J app.=6 Hz); 2.65 (t, 2H, J=6Hz); 2.30 (s, 3H). Microanalysis: C28H27O4NS Calc. % C=71.01 H=5.75 N=2.96 Found. % C=71.08 H=5.60 N=2.46

Workup

  1. customYield: 56% (purification by flash chromatography, eluent: ether/petroleum ether 6/4) m.p. 79° C

Sources & evidence

ORD record
ord-286b8c05ec6441d9b0802e128441de50
Source dataset
uspto-grants-1997_03
Patent number
US05612371

Reaction notes

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