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

HRID 890277Notes

Reaction equation

HRID 890277 reaction equation
[OH:1][NH:2][C:3]([CH:5]1[CH2:7][CH2:6]1)=[NH:4].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[N:19]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:18]([CH2:30][CH2:31][C:32](O)=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1>>[CH:5]1([C:3]2[N:4]=[C:32]([CH2:31][CH2:30][CH:18]3[CH2:17][CH2:16][CH:15]([C:12]4[CH:11]=[CH:10][C:9]([F:8])=[CH:14][CH:13]=4)[N:19]3[S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[O:1][N:2]=2)[CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 22250477(2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acidHCID 178513214HCID 178513214, compound

Product 1

HCID 22250470(2RS,5SR)-3-Cyclopropyl-5-{2-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-ethyl}-[1,2,4]oxadiazole

Procedure

The title compound, white solid, m.p. 129° C. and MS: m/e=456.4 (M+) was prepared in accordance with the general method of example 13 from N-hydroxy-cyclopropane-carboxamidine and (2RS,5SR)-3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid.

Sources & evidence

ORD record
ord-810e66f929de4b9abff8a0187a4d3cf3
Source dataset
uspto-grants-2006_02
Patent number
US06995182B2

Reaction notes

Loading…