N-(4-Amino-2-phenylbenzoyl)methionine methyl ester → [4-(N-tert-butoxycarbonyl-(R)-thiazolidin-4-ylmethyl)amino-2-phenylbenzoyl]methionine methyl ester

HRID 383116Notes

Reaction equation

HRID 383116 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH:13]=O)[CH2:11][S:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][C:17](=[O:39])[C@H:18]([CH2:35][CH2:36][S:37][CH3:38])[NH:19][C:20](=[O:34])[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH3:15][O:16][C:17](=[O:39])[C@H:18]([CH2:35][CH2:36][S:37][CH3:38])[NH:19][C:20](=[O:34])[C:21]1[CH:26]=[CH:25][C:24]([NH:27][CH2:13][C@@H:12]2[CH2:11][S:10][CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:23][C:22]=1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 18666758N-(4-Amino-2-phenylbenzoyl)methionine methyl ester2×HCID 20699040N-tert-butoxycarbonyl-(R)-(-)thiazolidine-4-carboxaldehyde

Product 1

HCID 54554572[4-(N-tert-butoxycarbonyl-(R)-thiazolidin-4-ylmethyl)amino-2-phenylbenzoyl]methionine methyl ester

Procedure

N-tert-butoxycarbonyl-(R)-(−)thiazolidine-4-carboxaldehyde was reductively aminated with 4-amino-2-phenylbenzoyl methionine methyl ester (compound 8) according to the procedure of Example 158B.

Sources & evidence

ORD record
ord-ee0c4085a93649f5bf7eb66f8693ea6e
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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