(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one → (5r)-3-[3-Fluoro-4-(1 (r,s)-oxo-3,6-dihydro-2h-thiopyran-4-yl)phenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723805Notes

Reaction equation

HRID 723805 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]4[CH:23]=[CH:22][N:21]=[N:20]4)[O:15][C:14]3=[O:24])=[CH:9][C:8]=2[F:25])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:27].[Na+]>CO.C(OCC)(=O)C.O>[F:25][C:8]1[CH:9]=[C:10]([N:13]2[CH2:17][C@H:16]([CH2:18][N:19]3[CH:23]=[CH:22][N:21]=[N:20]3)[O:15][C:14]2=[O:24])[CH:11]=[CH:12][C:7]=1[C:4]1[CH2:5][CH2:6][S:1](=[O:27])[CH2:2][CH:3]=1

Participants

6

Reactant 2

HCID 11302859(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-oneHCID 23667635Sodium periodate

Product 1

HCID 11451677(5r)-3-[3-Fluoro-4-(1 (r,s)-oxo-3,6-dihydro-2h-thiopyran-4-yl)phenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-oneYield 87.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one (Example 83; 1.25 g, 3.5 mmol) was stirred in a mixture of methanol and ethyl acetate (1:1, 50 ml) at ambient temperature. Sodium periodate (0.93 g, 4.3 mmol) in water (10 ml) was added dropwise, and it was stirred for 18 hours. Precipitated salts were removed by filtration and solvents were removed under vacuum. The residue was chromatographed on silica gel, washing with 25% acetone in dichloromethane, then eluting with 5 to 7% methanol in dichloromethane to give the title product (1.152 g).

Workup

  1. customPrecipitated salts were removed by filtration and solvents
  2. customwere removed under vacuum
  3. customThe residue was chromatographed on silica gel
  4. washwashing with 25% acetone in dichloromethane
  5. washeluting with 5 to 7% methanol in dichloromethane

Sources & evidence

ORD record
ord-f752ca4ffba34a81b583cd02910d6f3d
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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