Water → HCID 22022975, compound

HRID 1793668Notes

Reaction equation

HRID 1793668 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][OH:15])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][O:15][S:24]([CH3:23])(=[O:26])=[O:25])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22022982HCID 22022982, compound

Product 1

HCID 22022975HCID 22022975, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5RS)-3-(3,4-Difluorophenyl)-5-hydroxymethyl-4,5-dihydroisoxazole (3.79 g, 17.8 mM) was dissolved in anhydrous dichloromethane (200 ml) under a nitrogen atmosphere, cooled to 0°, and treated with triethylamine (2.51 g, 24.9 mM). Methanesulfonyl chloride (2.45 g, 21.4 mM) was added dropwise with stirring during a period of 30 minutes, then the mixture allowed to come to ambient temperature over 2 hours. The mixture was treated with water (200 ml), the organic layer separated, and washed with aqueous hydrochloric acid (2N, 100 ml), sodium bicarbonate (100 ml), and brine (200 ml). After drying (magnesium sulfate) and evaporation, the desired product was obtained as a white solid (4.85 g).

Workup

  1. temperaturecooled to 0°
  2. waitto come to ambient temperature over 2 hours
  3. customthe organic layer separated
  4. washwashed with aqueous hydrochloric acid (2N, 100 ml), sodium bicarbonate (100 ml), and brine (200 ml)
  5. customAfter drying
  6. custom(magnesium sulfate) and evaporation

Sources & evidence

ORD record
ord-8e277358f90547e089c61daadae3a19a
Source dataset
uspto-grants-2006_07
Patent number
US07081538B1

Reaction notes

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