Hydrochloric Acid → HCID 14800369, compound

HRID 1769866Notes

Reaction equation

HRID 1769866 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:39]=[CH:40][C:41]=1[O:42]C(=O)C)[CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][CH:11]([NH:26][C:27]([C:29]2[NH:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])[C:10]1=[O:38])(=O)C.CO.C(=O)([O-])[O-].[K+].[K+].Cl>O.C(OCC)(=O)C.O1CCCC1>[OH:4][C:5]1[CH:6]=[C:7]([CH:39]=[CH:40][C:41]=1[OH:42])[CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][CH:11]([NH:26][C:27]([C:29]2[NH:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])[C:10]1=[O:38]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 20097489HCID 20097489, compound

Product 1

HCID 14800369HCID 14800369, compoundYield 62.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3RS)-1-(3,4-diacetoxybenzyl)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-2H-1,4-benzodiazepine-2-one (287 mg), methanol (5 ml), tetrahydrofuran (5 ml), water (1 ml) and 1N aqueous potassium carbonate (5 ml) was stirred for 1.0 hour at 0°-5° C. and then adjusted to pH 1-2 with 6N hydrochloric acid. Ethyl acetate (50 ml) and water (50 ml) were added to the mixture under stirring. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel with an eluent of a mixture of chloroform and ethyl acetate (4:1) to give (3RS)-1-(3,4-dihydroxybenzyl)-3-(2-indolylcarbonylamino)-5-phenyl-2H-1,4-benzodiazepine-2-one (155 mg).

Workup

  1. stirringunder stirring
  2. washThe separated organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel with an eluent of a mixture of chloroform and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-0591266874b241a5b24b9941ae4543c0
Source dataset
uspto-grants-1995_01
Patent number
US05382664

Reaction notes

Loading…