홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Sodium hydride → (3RS)-1-(2-acetylthiophen-3-yl)methyl-3-tert-butoxycarbonylamino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one

HRID 1596339
노트
인쇄 미리보기

반응식

HRID 1596339 반응식
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][CH:11]1[N:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[C:15]2[CH:21]=[CH:22][CH:23]=[CH:24][C:14]=2[NH:13][C:12]1=[O:25])=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:26]([C:29]1[S:30][CH:31]=[CH:32][C:33]=1[CH2:34]Br)(=[O:28])[CH3:27]>CN(C)C=O>[C:26]([C:29]1[S:30][CH:31]=[CH:32][C:33]=1[CH2:34][N:13]1[C:14]2[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=2[C:16]([CH:18]([CH3:19])[CH3:20])=[N:17][CH:11]([NH:10][C:8]([O:7][C:3]([CH3:5])([CH3:6])[CH3:4])=[O:9])[C:12]1=[O:25])(=[O:28])[CH3:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 217012741-[3-(Bromomethyl)thiophen-2-yl]ethan-1-oneHCID 136152314(3RS)-3-tert-butoxycarbonylamino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one

생성물 1

HCID 21701415(3RS)-1-(2-acetylthiophen-3-yl)methyl-3-tert-butoxycarbonylamino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one수율 52.1%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
3회

실험 절차

To a suspension of sodium hydride (0.065 g of a 65% dispersion in mineral oil) in dry N,N-dimethylformamide (5 ml) was added dropwise a solution of (3RS)-3-tert-butoxycarbonylamino-2,3-dihydro-5-isopropyl-1H-1, 4-benzodiazepin-2-one (0.508 g) in dry N,N-dimethylformamide (5 ml) under cooling in an ice-bath. The mixture was stirred under the same condition for 30 minutes and then at ambient temperature for 2 hours. To the mixture was added dropwise a solution of 2-acetyl-3-bromomethylthiophene (0.420 g) in dry N,N-dimethylformamide under cooling in an ice-bath. After completion of the addition, the mixture was stirred under the same condition for 30 minutes and then at ambient temperature overnight. The resultant mixture was concentrated in vacuo. The residue was treated with ethyl acetate (100 ml), washed with water (50 ml) and dried over anhydrous sodium sulfate. Filtration and evaporation gave a crude product. The product was purified by column chromatography on silica gel with an eluent of a mixture of chloroform and ethyl acetate (10: 1) to give (3RS)-1-(2-acetylthiophen-3-yl)methyl-3-tert-butoxycarbonylamino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one (0.380 g).

후처리

  1. temperatureunder cooling in an ice-bath
  2. waitat ambient temperature for 2 hours
  3. temperatureunder cooling in an ice-bath
  4. additionAfter completion of the addition
  5. stirringthe mixture was stirred under the same condition for 30 minutes
  6. customat ambient temperature
  7. customovernight
  8. concentrationThe resultant mixture was concentrated in vacuo
  9. additionThe residue was treated with ethyl acetate (100 ml)
  10. washwashed with water (50 ml)
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationFiltration and evaporation
  13. customgave a crude product
  14. customThe product was purified by column chromatography on silica gel with an eluent of a mixture of chloroform and ethyl acetate (10: 1)

출처 및 근거

ORD 기록
ord-29ad3d4183584d67a6cb7e750acaab03
출처 데이터셋
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06291452B1

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트