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

HRID 1452593Notes

Reaction equation

HRID 1452593 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+:2]=[N-:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:46][C:47]1NN=N[N:48]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1.CO>[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][N:1]4[N:2]=[N:3][C:47]([CH3:46])=[N:48]4)[O:9][C:8]3=[O:10])=[CH:12][C:13]=2[F:26])[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86598351HCID 86598351, compoundHCID 178434708HCID 178434708, compound

Product 1

HCID 10365074(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-[(5-methyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-oneYield 56.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-(hydroxymethyl)-oxazolidin-2-one (WO 01/81350 A1) (0.50 g, 1.39 mmol), triphenylphosphine (0.55 g, 2.1 mmol), and 5-methyl-1H-tetrazole (0.18 g, 2.14 mmol) were dissolved in dry tetrahydrofuran (5 ml), and cooled on an ice-water bath. Diisopropylazodicarboxylate (0.41 ml, 2.58 mmol) was added dropwise and the mixture was stirred at 0° C. for 4 hours. Methanol (3 ml) was added, followed by evaporation of the solvent under reduced pressure and purification by flash column chromatography on silica gel with 10% acetonitrile in dichloromethane. The material obtained after chromatography was precipitated from dichloromethane with diethyl ether to give the title compound (0.335 g).

Workup

  1. temperaturecooled on an ice-water bath
  2. customfollowed by evaporation of the solvent under reduced pressure and purification by flash column chromatography on silica gel with 10% acetonitrile in dichloromethane
  3. customThe material obtained after chromatography
  4. customwas precipitated from dichloromethane with diethyl ether

Sources & evidence

ORD record
ord-47be601a4ca346429825bc82092031a7
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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