Sodium periodate → HCID 69583539, compound

HRID 723814Notes

Reaction equation

HRID 723814 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[N:24]=[CH:23][CH: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[N:24]=[CH:23][CH: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 69363345HCID 69363345, compound

Product 1

HCID 69583539HCID 69583539, compoundYield 74.1%

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-2-ylmethyl)oxazolidin-2-one (Example 88; 0.48 g, 1.3 mmol) was stirred in a mixture of methanol and ethyl acetate (1:1, 20 ml) at ambient temperature. Sodium periodate (0.28 g, 1.4 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. Crystallisation from dichloromethane gave the title compound (0.38 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. customCrystallisation from dichloromethane

Sources & evidence

ORD record
ord-6b93d943e2ac49ff8fbd616e621c91d9
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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