Water → HCID 86663474, compound

HRID 446593Notes

Reaction equation

HRID 446593 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@:9]([OH:22])([CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C.O>C(Cl)Cl.C(OCC)(=O)C>[CH3:23][S:24]([O:11][CH2:10][C@@:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Br:1])[CH:3]=1)([OH:22])[CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:19])([CH3:21])[CH3:20])([CH3:16])[CH3:17])(=[O:26])=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66688271HCID 66688271, compound

Product 1

HCID 86663474HCID 86663474, compoundYield 110.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (1.50 g, 3.80 mmol) obtained in Example 91d was dissolved in methylene chloride (60 mL), the mixture was stirred under ice cooling, methanesulfonyl chloride (0.35 mL, 4.56 mmol) and triethylamine (0.79 mL, 5.70 mmol) were added, and the mixture was stirred at the same temperature under a nitrogen atmosphere for 4 hours. After the reaction was completed, water was added to the reaction mixture under ice cooling, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a crude title compound (1.98 g) as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred at the same temperature under a nitrogen atmosphere for 4 hours
  2. customto separate the layers
  3. customThe resulting organic layer was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fcd50cb4525646fda217b313c6703241
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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