Triphenylphosphine → (5S)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-(aminomethyl)-oxazolidin-2-one

HRID 1452560Notes

Reaction equation

HRID 1452560 reaction equation
[N:1]([CH2:4][C@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([C:18]3[CH2:19][CH2:20][S:21](=[O:25])(=[O:24])[CH2:22][CH:23]=3)=[C:13]([F:26])[CH:12]=2)[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C(#N)C>[O:25]=[S:21]1(=[O:24])[CH2:20][CH:19]=[C:18]([C:14]2[C:15]([F:17])=[CH:16][C:11]([N:7]3[CH2:6][C@H:5]([CH2:4][NH2:1])[O:9][C:8]3=[O:10])=[CH:12][C:13]=2[F:26])[CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86598351HCID 86598351, compound

Product 1

HCID 57526977(5S)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-(aminomethyl)-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(5S)-5-(Azidomethyl)-3-[4-(1,1-dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-1,3-oxazolidin-2-one (WO 01/81350 A1) (7 g, 18.2 mmol) was dissolved in water (15 ml) and acetonitrile (150 ml). Triphenylphosphine (5.73 g, 21.9 mmol) was added and the resulting mixture was stirred at room temperature for 2 hours. The solvent was evaporated and the residue purified by flash column chromatography on silica gel with 5% methanol in dichloromethane. The fractions containing product were evaporated to near dryness and treated with ethereal HCl to precipitate the hydrochloride salt of the title compound as a white solid (5.03 g, 70%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by flash column chromatography on silica gel with 5% methanol in dichloromethane
  3. additionThe fractions containing product
  4. customwere evaporated
  5. additiontreated with ethereal HCl
  6. customto precipitate the hydrochloride salt of the title compound as a white solid (5.03 g, 70%)

Sources & evidence

ORD record
ord-2a31c9954105479189ca8577e2e3cf79
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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