Dimethyl Sulfide → HCID 86591695, compound

HRID 750901Notes

Reaction equation

HRID 750901 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][CH:10]=2)[CH2:5][CH:4]1[F:25].CSC.C(Cl)(=O)C>O1CCCC1>[O:2]=[C:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[CH:11][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:13][CH:14]=2)[CH2:5][CH:4]1[F:25]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 6367Acetyl chlorideHCID 86591692HCID 86591692, compound

Product 1

HCID 86591695HCID 86591695, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To the mixture of (S)-{3-[4-(4,4-dimethoxy-3-fluoropiperidin-1-yl)-phenyl]-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 tetrahydrofuran (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 67% 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-0b4f4d235b264244851391c394ce0bd4
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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