Water → 5-(S)-Aminomethyl-3-[4'-(N-methoxyamino)carbonvl-3'-fluorophenyl]-oxazolidine-2-one

HRID 2305664Notes

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]([NH:38][O:39][CH3:40])=[O:37])=[C:32]([F:41])[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]([NH:38][O:39][CH3:40])=[O:37])=[C:32]([F:41])[CH:31]=2)[CH2:25]1

Participants

Conditions

Temperature: 40 °C

Procedure

Triphenylphosphine (317 mg, 1.2 mmol) was added to a solution of 5-(S)-azidomethyl-3-[4′-(N-methoxyamino)carbonyl-3′-fluorophenyl]-oxazolidine-2-one. (0.335 g, 1.1 mmol) in THF (8 ml) under nitrogen atmosphere. The solution was stirred at 40° C. for 2 h, water (0.24 ml) was added, and the reaction mixture 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 (120 mg, 42%). HPLC Rt=3.5 min. MS (m/z): [M+H]+=284.

Workup

stirringthe reaction mixture 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-8094c625d6ba485eb37716f6e8549f96
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441005B1

Reaction notes

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