Acetic Acid → HCID 59543142, compound

HRID 1970973Notes

Reaction equation

HRID 1970973 reaction equation
[CH:1]1([CH:4]([NH:17][S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[C:5]([F:16])([F:15])S(C2C=CC=CC=2)(=O)=O)[CH2:3][CH2:2]1.CC([O-])=O.[Na+].CC(O)=O.[Mg]>CN(C=O)C.O>[CH:1]1([CH:4]([NH:17][S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH:5]([F:16])[F:15])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 5462224MagnesiumHCID 59543160N-[1-Cyclopropyl-2,2-difluoro-2-(phenylsulfonyl)ethyl]-2-methyl-2-propanesulfinamide

Product 1

HCID 59543142HCID 59543142, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[1-cyclopropyl-2,2-difluoro-2-(phenylsulfonyl)ethyl]-2-methylpropane-2-sulfinamide (0.8 g, 2.2 mmol) in DMF (30 mL) was added a solution of NaOAc (4.5 g, 55 mmol) in AcOH (4.5 g, 75 mmol) and H2O (7.0 mL). Magnesium turning (0.8 g, 33 mmol) was added in portions at room temperature under a water bath. The reaction mixture was stirred at room temperature overnight. Water (90 mL) was added to the solution, and the aqueous layer was extracted with EtOAc. The combined organics were washed with sat. NaHCO3, dried, concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (400 MHz, CDCl3) 5.75 (t, 1H); 3.50 (d, 1H); 2.58-2.70 (m, 1H); 1.18 (s, 9H); 0.90-1.00 (m, 1H); 0.58-0.70 (m, 2H); 0.35-0.50 (m, 2H).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined organics were washed with sat. NaHCO3
  3. customdried
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-88c8c1f7b7e64375866d3a73d5e64a67
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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