Dimethyl Sulfoxide → HCID 178444508, compound

HRID 2301249Notes

Reaction equation

HRID 2301249 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH:12]([C@H:22]1[CH2:27][CH2:26][C@H:25]([C@H:28]2[CH2:33][CH2:32][C@H:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:30][CH2:29]2)[CH2:24][CH2:23]1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1.C(N(CC)CC)C>C(Cl)Cl.O>[O:11]=[C:12]([C@H:22]1[CH2:27][CH2:26][C@H:25]([C@H:28]2[CH2:33][CH2:32][C@H:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:30][CH2:29]2)[CH2:24][CH2:23]1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178444509HCID 178444509, compound

Product 1

HCID 178444508HCID 178444508, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2.34 ml (33 mmol) of dimethyl sulfoxide were added at −60° under stirring in an argon atomosphere to a solution of 1.44 ml (16.5 mmol) of oxalyl chloride in 38 ml of methylene chloride and then a solution of 5.89 g (15 mmol) of 1-hydroxy-1-[trans-4-(trans-4-pentylcyclohexyl)cyclohexyl]-2-(3,4-difluorophenyl)ethane in 160 ml of methylene chloride was added over a period of 1 hr. After 15 minutes, 10.45 ml (75 mmol) of triethylamine were added and stirred for 2 hours and 50 minutes, and gradually raised to room temperature. 75 ml of water were added to stop the reaction. An organic layer and an aqueous layer were separated, the aqueous layer was extracted with methylene chloride, an extract combined with the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off and the concentrate was purified by column chromatography (elution solvent: toluene:heptane=2:1). Further, the eluate was recrystallized from heptane-solmix and toluene-solmix to obtain 4.83 g of the title compound (82%, Cr 111.9-112.8 Iso).

Workup

  1. customthe reaction
  2. customAn organic layer and an aqueous layer were separated
  3. extractionthe aqueous layer was extracted with methylene chloride
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe concentrate was purified by column chromatography (elution solvent: toluene:heptane=2:1)
  7. customFurther, the eluate was recrystallized from heptane-solmix and toluene-solmix

Sources & evidence

ORD record
ord-d1a817fe0f9643a0a9d151fb66509138
Source dataset
uspto-grants-2002_12
Patent number
US06500503B2

Reaction notes

Loading…