5-[1-(Thiazol-2-yl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoic acid → tert-Butyl (2S)-2-{5-[1-(thiazol-2-yl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino)-4-methylsulfonylbutyrate

HRID 1251899Notes

Reaction equation

HRID 1251899 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:18]([CH:22]=1)[C:19](O)=[O:20])[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.[NH2:32][C@@H:33]([CH2:41][CH2:42][S:43]([CH3:46])(=[O:45])=[O:44])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[C:18]([CH:22]=1)[C:19]([NH:32][C@@H:33]([CH2:41][CH2:42][S:43]([CH3:46])(=[O:45])=[O:44])[C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])=[O:20])[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

3

Reactant 2

HCID 183244285-[1-(Thiazol-2-yl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoic acidHCID 86585138Tert-butyl (2S)-2-amino-4-methanesulfonylbutanoate

Product 1

HCID 9809803tert-Butyl (2S)-2-{5-[1-(thiazol-2-yl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino)-4-methylsulfonylbutyrateYield 75%

Procedure

The title compound was prepared in 75% yield from 5-[1-(thiazol-2-yl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoic acid and L-methionine sulphone tert-butyl ester by similar methodology to that used for Example 40.

Sources & evidence

ORD record
ord-7a3b9d9193e74c46b41e9d9907c722b6
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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