Sodium periodate → HCID 58746164, compound

HRID 723812Notes

Reaction equation

HRID 723812 reaction equation
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:12]([F:13])=[CH:11][C:10]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:9][C:8]=2[F:26])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:28].[Na+]>CO.C(OCC)(=O)C.O>[F:13][C:12]1[CH:11]=[C:10]([N:14]2[CH2:18][C@H:17]([CH2:19][N:20]3[CH:24]=[CH:23][N:22]=[N:21]3)[O:16][C:15]2=[O:25])[CH:9]=[C:8]([F:26])[C:7]=1[C:4]1[CH2:5][CH2:6][S:1](=[O:28])[CH2:2][CH:3]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 58746163HCID 58746163, compound

Product 1

HCID 58746164HCID 58746164, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one (Example 86; 0.86 g, 2.3 mmol) was stirred in a mixture of methanol and ethyl acetate (1:1, 20 ml) at ambient temperature. Sodium periodate (0.50 g, 2.4 mmol) in water (10 ml) was added dropwise, and the mixture stirred for 3 hours. Precipitated salts were removed by filtration and washed with ethyl acetate. The filtrate was washed with brine, dried over magnesium sulfate and concentrated to dryness. The residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane to give the title product (0.69 g). MS (ESP): 395 (MH+) for C17H16F2N4O3S

Workup

  1. customPrecipitated salts were removed by filtration
  2. washwashed with ethyl acetate
  3. washThe filtrate was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-b17ce649a97c499d99b8194b7d455846
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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