Triethylamine → HCID 69204990, compound

HRID 748671Notes

Reaction equation

HRID 748671 reaction equation
C(N(CC)CC)C.CS(Cl)(=O)=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH:23]([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=2[F:36])[CH:24](O)[CH2:25][CH2:26][CH3:27])(=[O:22])=[O:21])=[CH:16][CH:15]=1>C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([C:23]([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=2[F:36])=[CH:24][CH2:25][CH2:26][CH3:27])(=[O:22])=[O:21])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23028680HCID 23028680, compound

Product 1

HCID 69204990HCID 69204990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

At 0° C., triethylamine (0.131 ml, 0.942 mmol) and methanesulfonyl chloride (0.0665 ml, 0.856 mmol) were added to a solution of 1-[(4-chlorophenyl)sulfonyl]-1-(2,5-difluorophenyl)-2-pentanol (204 mg, 0.544 mmol) in methylene chloride (10 ml). After stirring at 0° C. for 1 hour, the reaction mixture was diluted with methylene chloride, washed successively with a saturated aqueous ammonium chloride solution, water and brine, dried over MgSO4, and then concentrated. The residue was dissolved in tetrahydrofuran (5 ml). After cooling the solution to 0° C., potassium hexamethyldisilazide (a 0.5M toluene solution, 1.30 ml, 0.650 mmol) was added thereto. The resulting mixture was stirred at 0° C. for 3 hours, and saturated ammonium chloride was added thereto. The resulting mixture was extracted with ethyl acetate, washed successively with water and brine, dried over MgSO4, and then concentrated. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (15% ethyl acetate-hexane). The resulting solid was recrystallized from hexane, whereby the title compound (33.0 mg, 17%) was obtained as colorless needle crystals.

Workup

  1. washwashed successively with a saturated aqueous ammonium chloride solution, water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in tetrahydrofuran (5 ml)
  5. temperatureAfter cooling the solution to 0° C.
  6. additionpotassium hexamethyldisilazide (a 0.5M toluene solution, 1.30 ml, 0.650 mmol) was added
  7. stirringThe resulting mixture was stirred at 0° C. for 3 hours
  8. additionsaturated ammonium chloride was added
  9. extractionThe resulting mixture was extracted with ethyl acetate
  10. washwashed successively with water and brine
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated
  13. customThe residue thus obtained
  14. customwas purified by medium-pressure chromatography on a silica gel column (15% ethyl acetate-hexane)
  15. customThe resulting solid was recrystallized from hexane, whereby the title compound (33.0 mg, 17%)
  16. customwas obtained as colorless needle crystals

Sources & evidence

ORD record
ord-1fdf1da9a74e45338d46587485018b93
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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