Hydrochloric Acid → (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(E)-3-carboxy-2-propenyl]-5-phenyl-2H-1,4-benzodiazepine-2-one

HRID 1769863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1769863
[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]/[CH:31]=[CH:32]/[C:33]([O:35]C)=[O:34])[C:14]1=[O:37])=[O:11].O1CCCC1.[OH-].[Na+].Cl>C(OCC)(=O)C.O.CO>[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]/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34])[C:14]1=[O:37])=[O:11]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 20097493(3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(E)-3-methoxycarbonyl-2-propenyl]-5-phenyl-2H-1,4-benzodiazepine-2-one

Produkt 1

HCID 14800363(3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(E)-3-carboxy-2-propenyl]-5-phenyl-2H-1,4-benzodiazepine-2-oneAusbeute 17,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(E)-3-methoxycarbonyl-2-propenyl]-5-phenyl-2H-1,4-benzodiazepine-2-one (0.47 g), tetrahydrofuran (15 ml), methanol (7.5 ml) and 1N aqueous sodium hydroxide (1 ml) was stirred for 1.0 hour at room temperature and cooled. To the cooled reaction mixture were added water (100 ml) and ethyl acetate (100 ml) and the mixture was adjusted to pH 4.0 with 6N hydrochloric acid under stirring. The organic layer was separated, 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 methanol (1:1) to give (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino )-1-[(E)-3-carboxy-2-propenyl]-5-phenyl-2H-1,4-benzodiazepine-2-one (80 mg).

Aufarbeitung

  1. temperaturecooled
  2. customTo the cooled reaction mixture
  3. stirringunder stirring
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel with an eluent of a mixture of chloroform and methanol (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-fff5561f3b1242248f916c7c38716241
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05382664

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