5-(1-(4-Fluorophenyl)-2-(imidazol-1-yl)ethoxy)-2-(4-fluorophenethyl)benzoic acid → Cyclopentyl (2S)-2-{5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfanylbutyrate

HRID 1251888Notes

Reaction equation

HRID 1251888 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[C:20]([CH:24]=2)[C:21](O)=[O:22])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.[NH2:34][C@@H:35]([CH2:44][CH2:45][S:46][CH3:47])[C:36]([O:38][CH:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1)=[O:37]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[C:20]([CH:24]=2)[C:21]([NH:34][C@@H:35]([CH2:44][CH2:45][S:46][CH3:47])[C:36]([O:38][CH:39]2[CH2:40][CH2:41][CH2:42][CH2:43]2)=[O:37])=[O:22])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 183244905-(1-(4-Fluorophenyl)-2-(imidazol-1-yl)ethoxy)-2-(4-fluorophenethyl)benzoic acidHCID 53747326cyclopentyl (2S)-2-amino-4-(methylsulfanyl)butanoate

Product 1

HCID 9895783Cyclopentyl (2S)-2-{5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfanylbutyrateYield 72%

Procedure

The title compound was prepared in 72% yield from 5-(1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy)-2-(4-fluorophenethyl)benzoic acid and cyclopentyl (2S)-2-amino-4-(methylsulfanyl)butanoate (L-methionine cyclopentyl ester) by a similar method to that used for Example 34.

Sources & evidence

ORD record
ord-bea253e633224142b3201a75433732ae
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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