Pyridine → 1-Phthalimido-4-p-toluenesulfonyl-7,7-difluoro-8-methanesulfonyloxy-4-aza-octane

HRID 232167Notes

Reaction equation

HRID 232167 reaction equation
[C:1]1(=[O:32])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:10][CH2:11][C:12]([F:16])([F:15])[CH2:13][OH:14])[C:4](=[O:27])[C:3]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:2]12.N1C=CC=CC=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41].CC(C)=O.C1CCCCC1>ClCCl>[C:4]1(=[O:27])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)(=[O:18])=[O:19])[CH2:10][CH2:11][C:12]([F:16])([F:15])[CH2:13][O:14][S:40]([CH3:39])(=[O:42])=[O:41])[C:1](=[O:32])[C:2]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:3]12

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 139355851-Phthalimido-4-p-toluenesulfonyl-7,7-difluoro-8-hydroxy-4-aza-octaneHCID 21916603Acetone cyclohexane

Product 1

HCID 139355861-Phthalimido-4-p-toluenesulfonyl-7,7-difluoro-8-methanesulfonyloxy-4-aza-octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-phthalimido-4-p-toluenesulfonyl-7,7-difluoro-8-hydroxy-4-aza-octane (56.0 g, 120 mmoles) and dry pyridine (50 mL) in dry dichloromethane (400 mL), a solution of methanesulfonylchloride (14.4 g, 1.05 equivalents) in dichloromethane is added slowly at room temperature. After stirring overnight at room temperature, the mixture is washed with 1N HCl (500 mL), 10% aqueous NaHSO3 (250 mL), and water (250 mL). Drying (Na2SO4) and evaporation of the solvent yields an oil which solidifies under oil pump vacuum. Digestion with an acetone/cyclohexane mixture gives colorless crystals of 1-phthalimido-4-p-toluenesulfonyl-7,7-difluoro-8-methanesulfonyloxy-4-aza-octane.

Workup

  1. washthe mixture is washed with 1N HCl (500 mL), 10% aqueous NaHSO3 (250 mL), and water (250 mL)
  2. customDrying
  3. custom(Na2SO4) and evaporation of the solvent
  4. customyields an oil which

Sources & evidence

ORD record
ord-292c7899093f4b8e918ff45b63924d8d
Source dataset
uspto-grants-1989_07
Patent number
US04851448

Reaction notes

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