Water → 5-(S)-aminomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

HRID 351885Notes

Reaction equation

HRID 351885 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]([S:36]([CH3:38])=[O:37])=[C:32]([F:39])[CH:31]=2)[CH2:25]1)=[N+]=[N-].O>O1CCCC1>[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]([S:36]([CH3:38])=[O:37])=[C:32]([F:39])[CH:31]=2)[CH2:25]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 229662135-(S)-azidomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 229662005-(S)-aminomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-oneYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of triphenylphosphine (0.092 g, 0.352 mmol) and 5-(S)-azidomethyl-3-[4′-methylsulfinyl-3′-fluorophenyl]oxazolidine-2-one (0.100 g, 0.335 mmol) in tetrahydrofuran (2 ml) was stirred at r.t. for 4 h. Water (0.1 ml, 5.36 mmol) was added, and the mixture heated at 40° C. overnight. Solvent was evaporated under vacuum and the residue purified by PTLC (10% methanol in DCM) to give product as a white solid (0.082 g, 86%). MS (m/z): [M+H]+=273.

Workup

  1. temperaturethe mixture heated at 40° C. overnight
  2. customSolvent was evaporated under vacuum
  3. customthe residue purified by PTLC (10% methanol in DCM)

Sources & evidence

ORD record
ord-09cdd70a41b84c218ad661b7a7bb7dc2
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

Loading…