Dicyclohexylcarbodiimide → (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one

HRID 1769856노트

반응식

HRID 1769856 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]([OH:12])=O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[C:38]1([C:44]2[C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=3[N:48]([CH2:55][CH2:56][O:57][CH:58]3[CH2:63][CH2:62][CH2:61][CH2:60][O:59]3)[C:47](=[O:64])[CH:46]([NH2:65])[N:45]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)(Cl)Cl>[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:65][CH:46]1[N:45]=[C:44]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=2[N:48]([CH2:55][CH2:56][O:57][CH:58]2[CH2:63][CH2:62][CH2:61][CH2:60][O:59]2)[C:47]1=[O:64])=[O:12]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 14800304(3RS)-1,3-dihydro-5-phenyl-3-amino-1-{2-((RS)-2-tetrahydropyranyloxy) ethyl}-2H-1,4-benzodiazepine-2-one2회

생성물 1

HCID 14800305(3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one수율 76%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a mixture of indole-2-carboxylic acid (0.19 g), N-hydroxybenzotriazole (0.16 g) and N,N'-dicyclohexylcarbodiimide (0.24 g) in chloroform (10 ml) was added a mixture (0.43 g) of (3RS)-1,3-dihydro-5-phenyl-3-amino-1-{2-((RS)-2-tetrahydropyranyloxy) ethyl }-2H-1,4-benzodiazepine-2-one and (3RS)-1,3-dihydro-5-phenyl-3-amino-1-{2-((SR)-2-tetrahydropyranyloxy) ethyl }-2H-1,4-benzodiazepine-2-one at ambient temperature under stirring. The mixture was stirred for 2 hours under the same conditions. The resultant precipitate was filtered off. The combined filtrate and washings were evaporated under reduced pressure and the residual oil (1.20 g) was subjected to column chromatography on silica gel with an eluent of a mixture of chloroform and ethyl acetate (10:1) to give a mixture (white powder, 0.45 g) 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.

후처리

  1. stirringThe mixture was stirred for 2 hours under the same conditions
  2. filtrationThe resultant precipitate was filtered off
  3. customThe combined filtrate and washings were evaporated under reduced pressure
  4. additionthe residual oil (1.20 g) was subjected to column chromatography on silica gel with an eluent of a mixture of chloroform and ethyl acetate (10:1)

출처 및 근거

ORD 기록
ord-cfde013eeeef419da65d674dcefdf562
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05382664

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