Hydrochloric Acid → (RS)-N-(2,3-Dihydro-1-(2-hydroxyethyl)-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide

HRID 1769857ノート

反応式

HRID 1769857 の反応式
[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][CH2:31][O:32]C2CCCCO2)[C:14]1=[O:39])=[O:11].Cl.O>CC(C)=O>[OH:32][CH2:31][CH2:30][N:15]1[C:16]2[CH:29]=[CH:28][CH:27]=[CH:26][C:17]=2[C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:19][CH:13]([NH:12][C:10]([C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:11])[C:14]1=[O:39]

参加物

5

反応物 3

HCID 313Hydrochloric Acid2 回HCID 962WaterHCID 14800305(3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one2 回

生成物 1

HCID 14800306(RS)-N-(2,3-Dihydro-1-(2-hydroxyethyl)-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide収率 79.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a suspension of a mixture (0.42g)of (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino )-5-phenyl-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one and (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-{2-((SR)-2-tetrahydropyranyloxy) ethyl}-2H-1,4-benzodiazepine-2-one in acetone (10 ml) was added 6N-hydrochloric acid (0.4 ml) under stirring at ambient temperature. After the yellow clear solution was stirred for 45 minutes, the additional 6N-hydrochloric acid (0.4 ml) and water (1 ml) were added thereto. The mixture was stirred for 0.5 hour at ambient temperature. Neutralization with an aqueous solution of sodium bicarbonate and removal of acetone gave yellow precipitates, which were collected by filtration, washed with water and dried. The crude product was purified by column chromatography on silica gel with an eluent of a mixture of chloroform and ethyl acetate (5:1) to afford pure (3RS)-1,3-dihydro-1-(2-hydroxyethyl)-3-(2-indolylcarbonylamino )-5-phenyl-2H-1,4-benzodiazepine-2-one (0.28 g) as an amorphous. This was triturated in diethyl ether to give light yellow powder.

後処理

  1. stirringAfter the yellow clear solution was stirred for 45 minutes
  2. stirringThe mixture was stirred for 0.5 hour at ambient temperature
  3. customNeutralization with an aqueous solution of sodium bicarbonate and removal of acetone
  4. customgave yellow precipitates, which
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried
  8. customThe crude product was purified by column chromatography on silica gel with an eluent of a mixture of chloroform and ethyl acetate (5:1)

出典と根拠

ORDレコード
ord-1124abeeb6d446ebab2f32996ada4c83
出典データセット
uspto-grants-1995_01
特許番号
US05382664

反応ノート

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