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

HRID 1769863노트

반응식

HRID 1769863 반응식
[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]

참가 물질

8

반응물 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

생성물 1

HCID 14800363(3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-1-[(E)-3-carboxy-2-propenyl]-5-phenyl-2H-1,4-benzodiazepine-2-one수율 17.5%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-fff5561f3b1242248f916c7c38716241
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05382664

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