Sodium Acetate → HCID 15274845, compound

HRID 336150Notes

Reaction equation

HRID 336150 reaction equation
C([O-])(=O)C.[Na+].[OH:6][CH2:7][CH2:8][C@@H:9]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:10][CH2:11]S(C)=O>ClC1C=CC=CC=1Cl>[OH:6][CH2:7][CH2:8][C@@H:9]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 86711285HCID 86711285, compound

Product 1

HCID 15274845HCID 15274845, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
166 °C

Procedure

Sodium acetate (13.45 g) was added to a solution of tert-butyl ((3R)-1-hydroxy-5-(methylsulfinyl)pentan-3-yl)carbamate (9.38 g) obtained in Step 2 in 1,2-dichlorobenzene (140 ml) at room temperature. The mixture was stirred at an internal temperature of 166° C. for 18 hours. After cooling the reaction mixture, the insoluble matter was filtered off, and 1,2-dichlorobenzene was distilled off under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with a saturated aqueous sodium chloride solution, water, and a saturated sodium chloride solution; and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound 2.50 g as a light-yellow, oily substance.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe insoluble matter was filtered off
  3. distillation1,2-dichlorobenzene was distilled off under reduced pressure
  4. dissolutionThe resulting residue was dissolved in ethyl acetate
  5. washwashed with a saturated aqueous sodium chloride solution, water
  6. dry with materialand dried over anhydrous sodium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-061008d38a1f454f8290ab741de5c27e
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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