Dichloromethane methanol → HCID 86598979, compound

HRID 1816443Notes

Reaction equation

HRID 1816443 reaction equation
I([O-])(=O)(=O)=O.[Na+].[S:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[O:21][C:20]3=[O:33])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.C[OH:35].C(Cl)Cl>CO.O>[O:35]=[S:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[CH:15][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[O:21][C:20]3=[O:33])=[CH:17][CH:18]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 21226129Dichloromethane methanolHCID 23667635Sodium periodateHCID 86598978HCID 86598978, compound

Product 1

HCID 86598979HCID 86598979, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
4 °C

Procedure

Sodium periodate (1.7 g, 8.0 mmol) is added to a suspension of the product from Step 3 (3.0 g, 7.6 mmol) in 125 mL of 2:1 methanol:H2O. The mixture is stirred for 20 h at 4° C. in a cold room and then filtered to remove solids. The solids are washed with CHCl3 and the combined filtrate concentrated to give an aqueous solution that is diluted with H2O. This aqueous solution is extracted with five portions of CHCl3 and the combined organic extracts are dried (Na2SO4), filtered and concentrated to provide the crude product. Column chromatography (0-5% MeOH-DCM) provides the title compound as a foam. Step 5. Preparation of [[(5S)-3-[4-[2,3-dihydro-6-(trifluoroacetyl)-4H-1,4-thiazin-4-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]carbamic acid, 1,1-dimethylethyl ester.

Workup

  1. filtrationfiltered
  2. customto remove solids
  3. washThe solids are washed with CHCl3
  4. concentrationthe combined filtrate concentrated
  5. customto give an aqueous solution that
  6. extractionThis aqueous solution is extracted with five portions of CHCl3
  7. dry with materialthe combined organic extracts are dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto provide the crude product

Sources & evidence

ORD record
ord-2fe257601b4e47e582076a6d2b5d2b10
Source dataset
uspto-grants-2005_04
Patent number
US06884813B2

Reaction notes

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