(2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid → (2RS,5SR)-5-{2-[5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-ethyl}-3-methyl-[1,2,4]oxadiazole

HRID 890272Notes

Reaction equation

HRID 890272 reaction equation
[OH:1][NH:2][C:3](=[NH:5])[CH3:4].[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[N:17]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:16]([CH2:28][CH2:29][C:30](O)=O)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1>>[F:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]2[N:17]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)(=[O:19])=[O:20])[CH:16]([CH2:28][CH2:29][C:30]3[O:1][N:2]=[C:3]([CH3:4])[N:5]=3)[CH2:15][CH2:14]2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 22250477(2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acidHCID 178465666HCID 178465666, compound

Product 1

HCID 22250482(2RS,5SR)-5-{2-[5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-ethyl}-3-methyl-[1,2,4]oxadiazole

Procedure

The title compound, white solid, m.p. 91° C. and MS: m/e=430.5 (M+) was prepared in accordance with the general method of example 13 from N-hydroxy-acetamidine and (2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid, which was prepared in accordance with the general method of example 6a from (2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid methyl ester.

Sources & evidence

ORD record
ord-b3cf85021deb49f999a487437f9f3b12
Source dataset
uspto-grants-2006_02
Patent number
US06995182B2

Reaction notes

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