Water → (R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-pyrrolidin-2-one

HRID 273180Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH2:16][C@@H:15]([C:19]([NH:21][OH:22])=[NH:20])[CH2:14]2)=[CH:9][CH:8]=1.[C:26](Cl)(=O)[CH3:27].O>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:14][C@H:15]([C:19]3[N:20]=[C:26]([CH3:27])[O:22][N:21]=3)[CH2:16][C:17]2=[O:18])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-N-hydroxy-5-oxo-pyrrolidine-3-carboxamidine (0.020 g, 0.58 mmol) was dissolved in a mixture of 0.4 ml pyridine and acetyl chloride (0.01 ml, 0.116 mmol) was slowly added at 0° C. The mixture was then stirred at 70° C. overnight. Iced water was added and the mixture was stirred for one hour. Extraction with a saturated solution of ammonium chloride and dichloromethane gave the crude product that was purified by column cromatography on silica gel using a 19:1-mixture of dichloromethane and methanol as the eluent to obtain the title compound as a light yellow solid (0.0197 g, 92% of theory). MS (m/e)=368.4 (M+H)+.

Workup

additionwas slowly added at 0° C
stirringthe mixture was stirred for one hour
extractionExtraction with a saturated solution of ammonium chloride and dichloromethane
customgave the crude product that
customwas purified by column cromatography on silica gel using a 19

Sources & evidence

ORD record: ord-982dca934e85488fa20fd36976e4c0b4
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456210B2

Reaction notes

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