Tert-butyl (2S)-2-amino-4-(methylsulfanyl)butanoate → Tert-butyl (2S)-2-{2-(4-fluorophenyl)-4-[1-(thiazol-2-yl)-2-(imidazol-1-yl)ethoxymethyl]benzoylamino}-4-methylsulfanylbutyrate

HRID 1251874Notes

Reaction equation

HRID 1251874 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]([CH:17]([O:23][CH2:24][CH2:25][N:26]3[CH:30]=[CH:29][N:28]=[CH:27]3)[C:18]3[S:19][CH:20]=[CH:21][N:22]=3)[CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[CH:4][CH:3]=1.[C:31]([O:35][C:36](=[O:43])[C@H:37]([CH2:39][CH2:40][S:41][CH3:42])[NH2:38])([CH3:34])([CH3:33])[CH3:32]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]([CH:17]([O:23][CH2:24][CH2:25][N:26]3[CH:30]=[CH:29][N:28]=[CH:27]3)[C:18]3[S:19][CH:20]=[CH:21][N:22]=3)[CH:14]=[CH:13][C:9]=2[C:10]([NH:38][C@@H:37]([CH2:39][CH2:40][S:41][CH3:42])[C:36]([O:35][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:43])=[O:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7010638Tert-butyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 183244732-(4-Fluorophenyl)-4-[1-(thiazol-2-yl)-2-(imidazol-1-yl)ethoxymethyl]benzoic acid

Product 1

HCID 86585134Tert-butyl (2S)-2-{2-(4-fluorophenyl)-4-[1-(thiazol-2-yl)-2-(imidazol-1-yl)ethoxymethyl]benzoylamino}-4-methylsulfanylbutyrateYield 63%

Procedure

The title compound was prepared from 2-(4-fluorophenyl)4-[1-(thiazol-2-yl)-2-(imidazol-1-yl)ethoxymethyl]benzoic acid by a similar method to that used for Example 1 but using L-methionine tert-butyl ester in place of L-methionine methyl ester.

Sources & evidence

ORD record
ord-af1cc7d61edd4d6bbd6c2f6ecc105e19
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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