(4S)-3-acetyl-1,3-thiazolidine-4-carboxylic acid → N-Acetyl-D-thioproline 4-(trifluoromethyl)-DL-phenylalanine

HRID 1530941Notes

Reaction equation

HRID 1530941 reaction equation
C[O:2][C:3](=[O:17])[CH:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)[NH2:5].[C:18]([N:21]1[CH2:28][S:27][CH2:26][C@@H:22]1[C:23]([OH:25])=[O:24])(=[O:20])[CH3:19]>>[C:18]([N:21]1[CH2:28][S:27][CH2:26][C@@H:22]1[C:23]([OH:25])=[O:24])(=[O:20])[CH3:19].[F:14][C:13]([F:15])([F:16])[C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH:4]([C:3]([OH:17])=[O:2])[NH2:5])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 749158(4S)-3-acetyl-1,3-thiazolidine-4-carboxylic acidHCID 21253330Methyl 2-amino-3-(4-(trifluoromethyl)phenyl)propanoate

Product 1

HCID 131722413N-Acetyl-D-thioproline 4-(trifluoromethyl)-DL-phenylalanine

Procedure

from 4-(trifluoromethyl)-DL-phenylalanine methyl ester and N-acetyl-D-thioproline δH (DMSO-d6) 8.56-8.12 (1 H, m,NH), 7.68-7.55 (2 H, m, ArH), 7.51-7.37 (2 H, m, ArH),4.85-4.15 (4 H, m, NCH2S and 2×α-CH), 3.40-2.65 (4 H, m,SCH2CH and CH2Ar),2.06 (s) and 2.04 (s) and 1.80(s) and 1.71 (s); together (3 H, COCH3); m/z (ESI, 60 V), 391 (MH+).

Sources & evidence

ORD record
ord-cfacfe01dd6c4d95a66294b362a6579d
Source dataset
uspto-grants-2001_03
Patent number
US06197794B1

Reaction notes

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