Hydrochloric Acid → (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(2-aminothiazol-4-yl)methyl]-5-phenyl-2H-1,4-benzodiazepine-2-one

HRID 1073714Notes

Reaction equation

HRID 1073714 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][CH:13]1[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH2:30][C:31]2[N:32]=[C:33]([NH:36]C(=O)C)[S:34][CH:35]=2)[C:14]1=[O:40])=[O:11].CO.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O.O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][CH:13]1[N:19]=[C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH2:30][C:31]2[N:32]=[C:33]([NH2:36])[S:34][CH:35]=2)[C:14]1=[O:40])=[O:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 14800361(3RS)-1,3-dihydro-3-(2-indolylcarbonyl-amino)-1-[(2-acetamidothiazol-4-yl)methyl]-5-phenyl-2H-1,4-benzodiazepine-2-one

Product 1

HCID 14800362(3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(2-aminothiazol-4-yl)methyl]-5-phenyl-2H-1,4-benzodiazepine-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (3RS)-1,3-dihydro-3-(2-indolylcarbonyl-amino) -1-[(2-acetamidothiazol-4-yl)methyl]-5-phenyl-2H-1,4-benzodiazepine -2-one, methanol (13 ml), tetrahydrofuran (8 ml) and conc. hydrochloric acid (0.8 ml) was stirred for 7.0 hours at 70° C., cooled and adjusted to pH 7.0 with aqueous solution of sodium bicarbonate. To the mixture were added water (100 ml) and ethyl acetate (100 ml) under cooling. 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 ethyl acetate and chloroform (2:1) to give (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino) -1-[(2-aminothiazol-4-yl)methyl]-5-phenyl -2H-1,4-benzodiazepine-2-one.

Workup

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

Sources & evidence

ORD record
ord-2151ee3efd634237b1903b360fd19f6a
Source dataset
uspto-grants-1990_11
Patent number
US04970207

Reaction notes

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