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

Thiophenol → (2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-N-(1-cyanocyclopropyl)-4-(phenylthio)pyrrolidine-2-carboxamide

HRID 1697733
노트
인쇄 미리보기

반응식

HRID 1697733 반응식
C1(S(O[C@H:11]2[CH2:15][C@@H:14]([C:16](=[O:23])[NH:17][C:18]3([C:21]#[N:22])[CH2:20][CH2:19]3)[N:13]([C:24]([C:26]3([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[CH2:28][CH2:27]3)=[O:25])[CH2:12]2)(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1.[C:47]1([SH:53])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CC(N(C)C)=O.O>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:26]2([C:24]([N:13]3[CH2:12][C@H:11]([S:53][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH2:15][C@H:14]3[C:16]([NH:17][C:18]3([C:21]#[N:22])[CH2:20][CH2:19]3)=[O:23])=[O:25])[CH2:28][CH2:27]2)=[CH:34][CH:33]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7969ThiophenolHCID 8028Tetrahydrofuran2회HCID 11430Potassium CarbonateHCID 86646867(3S,5S)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-5-(1-cyanocyclopropylcarbamoyl)pyrrolidin-3-yl Benzenesulfonate

생성물 1

HCID 67277395(2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-N-(1-cyanocyclopropyl)-4-(phenylthio)pyrrolidine-2-carboxamide
수율 101.5%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

반응 조건

온도
22 °C

실험 절차

To a suspension of (3S,5S)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-5-(1-cyanocyclopropylcarbamoyl)pyrrolidin-3-yl benzenesulfonate (example 457c; 200 mg) and potassium carbonate (134 mg) in dimethylacetamide (1 mL) was added at tetrahydrofuran (1.2 mL) at room temperature THF and benzenethiol (50.7 mg). The reaction mixture was stirred at 22° C. for 20 hr then poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The crude mixture was concentrated to dryness and purified by chromatography on silica gel to yield the title compound as a colorless oil (184 mg; 89%). MS (ESI): m/z=466.13 [M+H]+.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe crude mixture was concentrated to dryness
  6. custompurified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-44de6e0ec5d14a138b9c3166326cfdc1
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163793B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트