Hydrochloric Acid → HCID 69748636, compound

HRID 2301041Notes

Reaction equation

HRID 2301041 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([S:10]([CH2:13][C:14]([O:16]C)=[O:15])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:18][C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22].Cl>CO>[Cl:3][C:4]1[CH:9]=[C:8]([S:10]([CH2:13][C:14]([OH:16])=[O:15])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:18][C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54292998HCID 54292998, compound

Product 1

HCID 69748636HCID 69748636, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (2.5 ml of a 2M aqueous solution) was added to a stirred solution of (R)-N-[2-chloro-4-(methoxycarbonylmethylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 142) (0.36 g) in methanol (6 ml) and the mixture was stirred for 1 hour. Hydrochloric acid (3 ml of a 2M aqueous solution) was added and volatile material was removed by evaporation. Ethyl acetate (80 ml) was added and the mixture washed with brine (50 ml), dried and volatile material removed by evaporation. The residue was dissolved in DCM (50 ml), washed with saturated sodium hydrogen carbonate solution (100 ml). The aqueous layer was treated with hydrochloric acid (25 ml, 10% v/v) and extracted into ethyl acetate (2×100 ml) and dried. Volatile material was removed by evaporation to give the title compound (0.28 g) as a foam. NMR: 1.62 (s, 3H), 4.57 (s, 2H) 7.9 (d, 2H), 8.02 (s, 1H), 8.06 (s, 1H), 8.32 (d, 1H), 9.92 (s, 1H); MS (ESP−): 388.

Workup

  1. customvolatile material was removed by evaporation
  2. additionEthyl acetate (80 ml) was added
  3. washthe mixture washed with brine (50 ml)
  4. customdried
  5. customvolatile material removed by evaporation
  6. dissolutionThe residue was dissolved in DCM (50 ml)
  7. washwashed with saturated sodium hydrogen carbonate solution (100 ml)
  8. additionThe aqueous layer was treated with hydrochloric acid (25 ml, 10% v/v) and
  9. extractionextracted into ethyl acetate (2×100 ml)
  10. customdried
  11. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-b75435e623c249cdabb8a8890c5bd3ee
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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