Sodium Hydroxide → HCID 70124887, compound

HRID 1596343Notes

Reaction equation

HRID 1596343 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:10]([CH2:12][N:13]1[C:19]3[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([CH2:25][O:26]C(=O)C)=[N:16][CH:15]([NH:30][C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])[C:14]1=[O:41])=[O:11])[CH2:2]2.[OH-].[Na+]>C(O)C>[CH:5]12[CH2:8][CH2:9][CH:1]([CH2:7][CH2:6]1)[CH2:2][N:3]([C:10]([CH2:12][N:13]1[C:19]3[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([CH2:25][OH:26])=[N:16][CH:15]([NH:30][C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])[C:14]1=[O:41])=[O:11])[CH2:4]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54535690HCID 54535690, compound

Product 1

HCID 70124887HCID 70124887, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3RS)-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-3-benzyloxycarbonylamino-5-acetoxymethyl-9-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one (1.9 g) in ethanol (40 ml) was added 1N-sodium hydroxide solution (7 ml) under stirring at ambient temperature. The mixture was stirred for 20 minutes under the same conditions. After removal of the solvent water was added into the mixture, which was adjusted to pH 4 with a diluted hydrochloric acid and extracted with ethyl acetate twice. The combined extract was washed with water and dried over magnesium sulfate. Removal of the solvent gave (3RS)-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-3-benzyloxycarbonylamino-5-hydroxymethyl-9-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one as an amorphous mass (1.68 g, 95.3%).

Workup

  1. stirringThe mixture was stirred for 20 minutes under the same conditions
  2. customAfter removal of the solvent water
  3. additionwas added into the mixture, which
  4. extractionextracted with ethyl acetate twice
  5. extractionThe combined extract
  6. washwas washed with water
  7. dry with materialdried over magnesium sulfate
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-f93f801e48f84000a1786a120b3acd6c
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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