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

HRID 1073707ノート

反応式

HRID 1073707 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]([OH:12])=O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.NC1N=CC2C=CC=CC=2N(CCOC2CCCCO2)C1=O.[C:60]1([C:66]2[C:72]3[CH:73]=[CH:74][CH:75]=[CH:76][C:71]=3[N:70]([CH2:77][CH2:78][O:79][CH:80]3[CH2:85][CH2:84][CH2:83][CH2:82][O:81]3)[C:69](=[O:86])[CH:68]([NH2:87])[N:67]=2)[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=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:87][CH:68]1[N:67]=[C:66]([C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[C:72]2[CH:73]=[CH:74][CH:75]=[CH:76][C:71]=2[N:70]([CH2:77][CH2:78][O:79][CH:80]2[CH2:85][CH2:84][CH2:83][CH2:82][O:81]2)[C:69]1=[O:86])=[O:12]

参加物

7

反応物 5

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-oneHCID 70360821amino-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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 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.

後処理

  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)

出典と根拠

ORDレコード
ord-ff40c51532d449bc8529127a5cefbaa3
出典データセット
uspto-grants-1990_11
特許番号
US04970207

反応ノート

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