Dimethyl Sulfide → HCID 68700025, compound

HRID 1026656Notes

Reaction equation

HRID 1026656 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-f97ad2e59d6448e18e0102318b92363a
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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