Potassium Carbonate → (3S)-1-(2-hydroxyethyl)-3-(2-indolylcarbonylamino)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-one

HRID 1769859Notes

Reaction equation

HRID 1769859 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:10][C@H:9]([NH:24][C:25]([C:27]2[NH:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[C:8]1=[O:36])(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:4][CH2:5][CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:10][C@H:9]([NH:24][C:25]([C:27]2[NH:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[C:8]1=[O:36]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14800310HCID 14800310, compound

Product 1

HCID 14800307(3S)-1-(2-hydroxyethyl)-3-(2-indolylcarbonylamino)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-oneYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (3S)-1-(2-acetoxyethyl)-3-(2-indolylcarbonylamino)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-one (1.80 g) and potassium carbonate (0.30 g) in 85% aqueous ethanol (30 ml) was heated at 65° to 70° C. for 1 hour under stirring. After cooling, ethanol was removed under reduced pressure, and to the residue was added water. The aqueous mixture was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. Removal of the solvent afforded a light yellow amorphous powder, which was chromatographed on silica gel with an eluent of a mixture of chloroform and ethyl acetate (3:1). The fractions containing the desired product were combined and evaporated to give (3S)-1-(2-hydroxyethyl)-3-(2-indolylcarbonylamino)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-one (1.47 g) as a colorless amorphous powder.

Workup

  1. temperaturewas heated at 65° to 70° C. for 1 hour
  2. temperatureAfter cooling
  3. customethanol was removed under reduced pressure
  4. additionto the residue was added water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customRemoval of the solvent
  9. customafforded a light yellow amorphous powder, which
  10. customwas chromatographed on silica gel with an eluent of a mixture of chloroform and ethyl acetate (3:1)
  11. additionThe fractions containing the desired product
  12. customevaporated

Sources & evidence

ORD record
ord-960db06cf4f04627afe9741f3c0b4f40
Source dataset
uspto-grants-1995_01
Patent number
US05382664

Reaction notes

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