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

HRID 890264Notes

Reaction equation

[C:1]([OH:4])(=O)[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[N:28]([S:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[CH:27]([C:39]([NH:41]O)=[NH:40])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1>CN(C=O)C>[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[N:28]([S:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[CH:27]([C:39]3[N:40]=[C:1]([CH3:2])[O:4][N:41]=3)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of acetic acid (0.11 ml, 1.99 mmol), 1,1′-carbonyl-diimidazole (0.32 g, 1.99 mmol) in DMF (12 ml) was stirred at room temperature for 2 h and subsequently (2RS,5SR)-5-(4-fluoro-phenyl)-N-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxamidine (0.50 g, 1.32 mmol) was added. The reaction mixture was stirred at 80° C. for 16 h and evaporated. Acetic acid (10 ml) was added and the stirred mixture was heated under reflux conditions for 2 h. Aqueous work-up, column chromatography on silica gel (ethyl acetate/hexane 1:1) and crystallization from ethyl acetate/hexane yielded the title compound (0.36 g, yield 68%) as a white solid, m.p. 115° C. and MS: m/e=246.1 (M+H+).

Workup

customevaporated
additionAcetic acid (10 ml) was added
temperaturethe stirred mixture was heated under reflux conditions for 2 h
customAqueous work-up, column chromatography on silica gel (ethyl acetate/hexane 1:1) and crystallization from ethyl acetate/hexane

Sources & evidence

ORD record: ord-c3d553f4b3bc4b3bb1baf696eeb031ee
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995182B2

Reaction notes

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