Dimethyl Sulfide → HCID 68700025, compound

HRID 2247003Notes

Reaction equation

HRID 2247003 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][C:10]=2[F:26])[CH2:5][CH:4]1[F:27].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][C:10]=2[F:26])[CH2:5][CH:4]1[F:27]

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 6367Acetyl chlorideHCID 68698365HCID 68698365, compound

Product 1

HCID 68700025HCID 68700025, compoundYield 61%

Conditions

Temperature
40 °C

Procedure

The mixture of (S)-{3-[4-(4,4-dimethoxy-3-fluoropiperidin-1-yl)-3-fluorophenyl]-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 61% 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-acb6c6ebd1c74ad0a049899e611953ce
Source dataset
uspto-grants-2010_03
Patent number
US07687627B2

Reaction notes

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