Dimethyl Sulfoxide → HCID 131722213, compound

HRID 1275168Notes

Reaction equation

HRID 1275168 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]2[C@@H:24]([CH2:25][CH2:26][OH:27])[O:23][CH2:22][CH2:21][N:20]2[C:28](=[O:41])[C:29]2[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=2)[CH:15]=[CH:16][C:17]=1[Cl:18].C(N(CC)CC)C>C(Cl)Cl.O>[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]2[C@@H:24]([CH2:25][CH:26]=[O:27])[O:23][CH2:22][CH2:21][N:20]2[C:28](=[O:41])[C:29]2[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=2)[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 131722211HCID 131722211, compound

Product 1

HCID 131722213HCID 131722213, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

0.88 ml (10.1 mmole) of oxalyl chloride was dissolved in 10 ml of methylene chloride, and 5 ml of a methylene chloride solution containing 0.79 ml (11.1 mmole) of dimethyl sulfoxide were added dropwise to the resulting solution at -78° C. under a nitrogen atmosphere. The mixture was then stirred for 30 minutes. 10 ml of a methylene chloride solution containing 950 mg (2.02 mmole) of 2-[(2 R)-(3,4-dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanol [prepared as described in step (d) above] were added dropwise to the resulting mixture, and the mixture as stirred for 4 hours. At the end of this time, a further 2.24 ml (16.2 mmole) of triethylamine was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into water and extracted with methylene chloride. The organic extract was washed with water, and then with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of methylene chloride and acetone ranging from 23:2 to 21:4 by volume as the eluent, to give 878 mg of the title compound.

Workup

  1. additionwere added dropwise to the resulting solution at -78° C. under a nitrogen atmosphere
  2. additionwere added dropwise to the resulting mixture
  3. stirringthe mixture as stirred for 4 hours
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. extractionextracted with methylene chloride
  6. extractionThe organic extract
  7. washwas washed with water
  8. dry with materialwith a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customthe resulting residue was purified by silica gel column chromatography
  11. washa gradient elution method

Sources & evidence

ORD record
ord-72e15bb353314226a9ea1de3161feb4b
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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