Water → 4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-benzamide

HRID 351872Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C@H:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([NH2:38])=[O:37])=[C:32]([F:39])[CH:31]=2)[CH2:25]1)=[N+]=[N-].O>C1COCC1>[NH2:20][CH2:23][C@@H:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([NH2:38])=[O:37])=[C:32]([F:39])[CH:31]=2)[CH2:25]1

Participants

Conditions

Temperature: 40 °C

Procedure

Triphenylphosphine (2.9 g, 11.0 mmol) was added portionwise to a solution of 5-(S)-azidomethyl-3-[4′-aminocarbonyl-3′-fluorophenyl]oxazolidine-2-one (2.8 g, 10.0 mmol) in THF (75 ml) under nitrogen atmosphere. The solution was stirred at 40° C. for 2 h, water (2.0 ml) added, and the reaction mixture was stirred at 40° C. overnight. Solvent was removed under vacuum, and the resulting solid was triturated with ether. Precipitated material was filtered, washed with ether and ethanol and dried under vacuum to afford the product as white crystals (1.7 g, 69%). HPLC Rt=5.0 min. MS (m/z): [M+H]+=254.

Workup

stirringthe reaction mixture was stirred at 40° C. overnight
customSolvent was removed under vacuum
customthe resulting solid was triturated with ether
filtrationPrecipitated material was filtered
washwashed with ether and ethanol
customdried under vacuum

Sources & evidence

ORD record: ord-50aa5b50cbc64c178a50d6767ac66317
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743811B2

Reaction notes

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