Dimethyl Sulfide → HCID 69312990, compound

HRID 750917Notes

Reaction equation

HRID 750917 reaction equation
C[O:2][C:3]1(OC)[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[O:17][C:16]3=[O:25])=[CH:11][CH:10]=2)[CH2:5][C:4]1([F:27])[F:26].CSC.C(Cl)(=O)C>>[O:2]=[C:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[O:17][C:16]3=[O:25])=[CH:11][CH:10]=2)[CH2:5][C:4]1([F:27])[F:26]

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 6367Acetyl chlorideHCID 69312124HCID 69312124, compound

Product 1

HCID 69312990HCID 69312990, compoundYield 71%

Conditions

Temperature
40 °C

Procedure

The mixture of (S)-{3-[4-(4,4-dimethoxy-3,3-difluoropiperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.0 mmol), freshly fused zinc chloride (3.1 mmol), dimethyl sulphide (5.1 mmol), acetyl chloride (3.1 mmol) in tetrahydrofuaran (50 ml) was stirred at 40° C. for 4 days. The reaction mixture was extracted with ethyl acetate water mixture and the organic layer was dried over sodium sulfate. The removal of the solvent afforded a residue, which was chromatographed over silica gel to give title compound in 71% yield.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate water mixture
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customThe removal of the solvent
  4. customafforded a residue, which
  5. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-f7b36b85a6c84c959a04c1d02d6da216
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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