Methanesulfonyl chloride → HCID 58460218, compound

HRID 1946505Notes

Reaction equation

HRID 1946505 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:18]3[CH:19]([CH2:23][OH:24])[CH2:20][CH2:21][CH2:22][C:17]=3[N:16]=[C:15]2[CH:25]([CH3:27])[CH3:26])=[CH:9][CH:8]=1>ClCCl>[CH3:4][S:1]([O:24][CH2:23][CH:19]1[C:18]2[N:14]([CH2:13][C:10]3[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=3)[C:15]([CH:25]([CH3:26])[CH3:27])=[N:16][C:17]=2[CH2:22][CH2:21][CH2:20]1)(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58460150HCID 58460150, compound

Product 1

HCID 58460218HCID 58460218, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Mesyl chloride (0.874 mL) was added dropwise to a suspension of Intermediate 40 (2.98 g) in dichloromethane (100 mL) at 0° C. under N2. Once addition was complete, the reaction was allowed to stir at 0° C. for a further 30 minutes before the bath was removed and the solution warmed to RT. The reaction mixture was quenched with water, and the aqueous extracted with DCM. The combined organics were passed through a hydrophobic frit and concentrated under reduced pressure, azeotroped with MeOH and dried on the high-vac to give the title compound 3.44 g. LC/MS MH+ 397, Rt 1.78 min (5 minute run).

Workup

  1. additionOnce addition
  2. customwas removed
  3. temperaturethe solution warmed to RT
  4. customThe reaction mixture was quenched with water
  5. extractionthe aqueous extracted with DCM
  6. concentrationconcentrated under reduced pressure
  7. customazeotroped with MeOH
  8. customdried on the high-vac

Sources & evidence

ORD record
ord-8807508f07ed4380a3b2105cec81cbef
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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