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

HRID 351876Notes

Reaction equation

HRID 351876 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

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 229662155-(S)-azidomethyl-3-[4'-(N-methoxyamino)carbonyl-3'-fluorophenyl]-oxazolidine-2-one

Product 1

HCID 229662015-(S)-Aminomethyl-3-[4'-(N-methoxyamino)carbonvl-3'-fluorophenyl]-oxazolidine-2-oneYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

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

Sources & evidence

ORD record
ord-c1062337eb6f475d8ab49e0e853fb585
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

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