Methanol → HCID 25216458, compound

HRID 1929423Notes

Reaction equation

HRID 1929423 reaction equation
C([O:9][CH2:10][C:11]1[CH:16]=[C:15]([N:17]2[C:22]3[CH:23]=[CH:24][C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][C:21]=3[O:20][C:19]([CH3:33])([CH3:32])[C:18]2=[O:34])[CH:14]=[CH:13][C:12]=1[Cl:35])(=O)C1C=CC=CC=1.CO.[OH-].[Na+].[Cl-].[NH4+]>O1CCCC1>[Cl:35][C:12]1[CH:13]=[CH:14][C:15]([N:17]2[C:22]3[CH:23]=[CH:24][C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][C:21]=3[O:20][C:19]([CH3:33])([CH3:32])[C:18]2=[O:34])=[CH:16][C:11]=1[CH2:10][OH:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 66790987HCID 66790987, compound

Product 1

HCID 25216458HCID 25216458, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-5-{2,2-dimethyl-7-[(methylsulfonyl)amino]-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl}benzyl benzoate (compound obtained in Example 141; 80 mg) in tetrahydrofuran (3 mL)-methanol (3 mL) was added an aqueous 2N sodium hydroxide solution (0.39 mL) under ice-cooling, and the mixture was stirred at the same temperature for 8 hours. The reaction mixture was acidified with an aqueous saturated ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=7/3→2/3) and triturated with diisopropylether/n-hexane (1/1) to give N-{4-[4-chloro-3-(hydroxymethyl)phenyl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide (39 mg) as a colorless powder.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=7/3→2/3)
  7. customtriturated with diisopropylether/n-hexane (1/1)

Sources & evidence

ORD record
ord-a1b51e0483934de2b1ece715b85c196e
Source dataset
uspto-grants-2012_05
Patent number
US08188073B2

Reaction notes

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