Sodium Hydroxide → HCID 22329077, compound

HRID 586861Notes

Reaction equation

HRID 586861 reaction equation
[CH3:1][S:2]([N:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[CH:15][C:10]=2[CH:9]=[C:8]([C:28]([O:30]C)=[O:29])[CH2:7][CH2:6]1)(=[O:4])=[O:3].[OH-].[Na+]>CO.C1COCC1>[CH3:1][S:2]([N:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:20][CH:21]=3)=[CH:15][C:10]=2[CH:9]=[C:8]([C:28]([OH:30])=[O:29])[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 22329194HCID 22329194, compound

Product 1

HCID 22329077HCID 22329077, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In methanol (100 ml) and THF (100 ml) was dissolved methyl 1-methanesulfonyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.4 g). To the solution was added 1N sodium hydroxide solution (10 ml), and the mixture was stirred at room temperature overnight. To the mixture was added 1N sodium hydroxide solution (5 ml), and the mixture was stirred at 60° C. for 1.5 hours and concentrated. To the residue was added water, and the mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate, and the solvent was evaporated to give 1-methanesulfonyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.36 g) as pale yellow crystals.

Workup

  1. stirringthe mixture was stirred at 60° C. for 1.5 hours
  2. concentrationconcentrated
  3. additionTo the residue was added water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2a66141b1b034d4babfa53f6ba762f02
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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