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

4-Methylmorpholine → [(R)-3-diazo-1-(4-methoxy-benzylsulfanylmethyl)-2-oxo-propyl]-carbamic acid t-butyl ester

HRID 336445
노트
인쇄 미리보기

반응식

HRID 336445 반응식
C([C@@:8]([NH2:23])([CH2:12][S:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[C:9]([OH:11])=O)(OC(C)(C)C)=O.[CH3:24]N1CCOCC1.C(O[C:34](Cl)=[O:35])C.[OH-:37].[K+].[CH3:39][N:40]([N:44]=O)C(N)=O.O1[CH2:50][CH2:49][CH2:48]C1>O.C(OCC)C>[C:49]([O:37][C:34](=[O:35])[NH:23][C@@H:8]([CH2:12][S:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:9](=[O:11])[CH:39]=[N+:40]=[N-:44])([CH3:48])([CH3:50])[CH3:24]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 6

HCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium HydroxideHCID 68486000(R)-2-BOC-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid

생성물 1

HCID 86672690
[(R)-3-diazo-1-(4-methoxy-benzylsulfanylmethyl)-2-oxo-propyl]-carbamic acid t-butyl ester
수율 95%

시약·촉매·용매 2

HCID 962Water용매2회HCID 3283Diethyl Ether용매

반응 조건

온도
-25 °C

실험 절차

(R)-2-BOC-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid (43 g, 132 mmol) prepared in Step B, 1-methylmorpholine (14.5 mL, 132 mmol) and ethylchloroformate (14.1 mL, 132 mmol) were dissolved in tetrahydrofuran (500 mL), and the mixture was stirred for 1 h at −25° C. At the same time, potassium hydroxide (75 g, 1336 mmol) was dissolved in water (75 mL) and diethylether (750 mL), N-methyl-nitrosourea (26 g, 252 mmol) was added in drops thereto over 2 h at 0° C., and the mixture was stirred for 30 min. The two solutions thus obtained were mixed together, and stirred for 3 h at −25° C. to room temperature. After completion of the reaction, water was added to the reaction mixture, which was then washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous ammonium chloride solution in the order. The organic layer was concentrated to give the title compound (46.0 g, Yield 95%).

후처리

  1. waitover 2 h at 0° C.
  2. stirringthe mixture was stirred for 30 min
  3. customThe two solutions thus obtained
  4. additionwere mixed together
  5. stirringstirred for 3 h at −25° C. to room temperature
  6. additionwas added to the reaction mixture, which
  7. washwas then washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous ammonium chloride solution in the order
  8. concentrationThe organic layer was concentrated

출처 및 근거

ORD 기록
ord-81b1320c0299424cbca1f3cbf17faa69
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889691B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트