Dimethyl Sulfide → HCID 86591699, compound

HRID 750910Notes

Reaction equation

HRID 750910 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][N:21]=[N+:22]=[N-:23])[O:17][C:16]3=[O:24])=[CH:11][C:10]=2[F:25])[CH2:5][CH:4]1[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][N:21]=[N+:22]=[N-:23])[O:17][C:16]3=[O:24])=[CH:11][C:10]=2[F:25])[CH2:5][CH:4]1[F:26]

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 6367Acetyl chlorideHCID 86591696HCID 86591696, compound

Product 1

HCID 86591699HCID 86591699, compoundYield 69%

Conditions

Temperature
40 °C

Procedure

To the mixture of (S)-{3-[4-(4,4-dimethoxy-3-fluoropiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-azide (0.5 mmol), freshly fused zinc chloride (1.5 mmol), dimethyl sulphide (2.5 mmol), acetyl chloride (1.5 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 69% 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-acd42c2a8ba4426d855feb941df0a22e
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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