(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one → (5r)-3-[4-(1(r,s)-Oxo-3,6-dihydro-2h-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one

HRID 1452559Notes

Reaction equation

HRID 1452559 reaction equation
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:19]=[N+:20]=[N-:21])[O:15][C:14]3=[O:22])=[CH:9][C:8]=2[F:23])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:25].[Na+]>CO.C(OC(=O)C)C.O>[O:25]=[S:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:19]=[N+:20]=[N-:21])[O:15][C:14]3=[O:22])=[CH:9][C:8]=2[F:23])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 11450455(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-oneHCID 23667635Sodium periodate

Product 1

HCID 11371542(5r)-3-[4-(1(r,s)-Oxo-3,6-dihydro-2h-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-oneYield 95.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

(5R)-3-[4-(3,6-Dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one (2.3 g, 6.5 mmol) (see WO 01/81350) was dissolved in methanol/ethylacetate (1:1, 100 ml) and sodium periodate (1.75 g, 8.2 mmol), dissolved in water (20 ml) was added dropwise over 1 hour. The reaction mixture was stirred for 7 hours at room temperature, filtered to remove most of the salts and the methanol was evaporated under vacuum. The aqueous solution thus obtained was extracted with ethyl acetate, dried over sodium sulfate and it was evaporated to dryness. The residue was subjected to chromatography on silica gel with acetone/hexane (2:1) to give 2.18 g of the product.

Workup

  1. additionwas added dropwise over 1 hour
  2. filtrationfiltered
  3. customto remove most of the salts
  4. customthe methanol was evaporated under vacuum
  5. customThe aqueous solution thus obtained
  6. extractionwas extracted with ethyl acetate
  7. dry with materialdried over sodium sulfate and it
  8. customwas evaporated to dryness

Sources & evidence

ORD record
ord-6bc00d4735ab46149c9746eef821eb1e
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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