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

HRID 890267Notes

Reaction equation

HRID 890267 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]([C:23](O)=[O:24])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O[NH:27][C:28](=[NH:30])[CH3:29]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)(=[O:15])=[O:14])[CH:11]([C:23]3[O:24][N:30]=[C:28]([CH3:29])[N:27]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 22250450(2RS,5SR)-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acidHCID 178465666HCID 178465666, compound

Product 1

HCID 22250540(2RS,5SR)-5-[5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-3-methyl-[1,2,4]oxadiazole

Procedure

The title compound, off-white solid, m.p. 128° C. and MS: m/e=401.2 (M+) was prepared in accordance with the general method of example 13 from (2RS,5SR)-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid and N-hydroxy-acetamidine.

Sources & evidence

ORD record
ord-107082609112403595a3b4c833a09023
Source dataset
uspto-grants-2006_02
Patent number
US06995182B2

Reaction notes

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