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

HRID 2309593Notes

Reaction equation

HRID 2309593 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-d85b408c09ca4301a366ccd3a89b3420
Source dataset
uspto-grants-1987_09
Patent number
US04695654

Reaction notes

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