(R)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate → methyl(2R,4E)-4-[(2R)-1-{[{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinylidene]-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoate

HRID 472700

반응식

HRID 472700 반응식
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:33])[C:16]([N:18]2[CH2:23][CH2:22][C:21](=[CH2:24])[CH2:20][C@@H:19]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[CH3:32])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:36][C:37]([O:40][C:41]([NH:43][C@H:44]([CH2:49]C=C)[C:45]([O:47][CH3:48])=[O:46])=[O:42])([CH3:39])[CH3:38]>CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[F:35][C:2]([F:1])([F:34])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:33])[C:16]([N:18]2[CH2:23][CH2:22]/[C:21](=[CH:24]\[CH2:49][C@@H:44]([NH:43][C:41]([O:40][C:37]([CH3:36])([CH3:39])[CH3:38])=[O:42])[C:45]([O:47][CH3:48])=[O:46])/[CH2:20][C@@H:19]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[CH3:32])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

참가 물질

4

반응물 2

HCID 58169888(R)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoateHCID 58169930(2R)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-methylidene-1-piperidinecarboxamide2회

생성물 1

HCID 86684788methyl(2R,4E)-4-[(2R)-1-{[{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinylidene]-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoate

시약·촉매·용매 1

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)ruthenium촉매2회

반응 조건

온도
47 °C

실험 절차

A solution of (2R)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-methylidene-1-piperidinecarboxamide (intermediate 53 3 g, 5.97 mmol) and methyl (2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentenoate (4.11 g, 17.91 mmol) in dry, degassed dichloromethane (DCM) (24 ml), was added to a flame dried round bottomed flask containing (1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(o-isopropoxyphenylmethylene)ruthenium, Hoveyda-Grubbs catalyst 2nd generation, (0.187 g, 0.299 mmol) under a nitrogen atmosphere. The green mixture was stirred and heated at reflux for 30 h (T bath=47° C.).

후처리

  1. customdegassed dichloromethane (DCM) (24 ml)
  2. additionwas added to a flame
  3. customdried round bottomed flask
  4. temperatureheated

출처 및 근거

ORD 기록
ord-080afdc12ee847a38c7351a32cda1c18
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633214B2

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