Dimethyl Sulfide → HCID 59754175, compound

HRID 750908Notes

Reaction equation

HRID 750908 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][OH:21])[O:17][C:16]3=[O:22])=[CH:11][C:10]=2[F:23])[CH2:5][CH:4]1[F:24].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][OH:21])[O:17][C:16]3=[O:22])=[CH:11][C:10]=2[F:23])[CH2:5][CH:4]1[F:24]

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 6367Acetyl chlorideHCID 59754112HCID 59754112, compound

Product 1

HCID 59754175HCID 59754175, compoundYield 54%

Conditions

Temperature
40 °C

Procedure

To the mixture of (R)-{3-[4-(4,4-dimethoxy-3-fluoropiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-alcohol (0.726 mmol), freshly fused zinc chloride (2.17 mmol), dimethyl sulphide (3.2 mmol), acetyl chloride (2.17 mmol) in tetrahydrofuaran (50 ml) was stirred at 40° C. for 4 days. To this reaction mixture extracted with the ethyl acetate water mixture and organic layer was dried over sodium sulfate. The removal of the solvent afforded a residue, which was chromatographed over silica gel afforded title compound in 54% yield.

Workup

  1. extractionTo this reaction mixture extracted with the ethyl acetate water mixture and organic layer
  2. dry with materialwas 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-58da2ec550874e4ea00965ac0e49c305
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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