Tributylphosphine → Methyl 2-[4-({4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzyl}oxy)phenyl]cyclopropanecarboxylate

HRID 1691537노트

반응식

HRID 1691537 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[CH3:15][CH:16]([CH3:44])[CH2:17][CH2:18][N:19]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42]O)=[CH:38][CH:37]=1)[C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[N:24]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[CH3:15][CH:16]([CH3:44])[CH2:17][CH2:18][N:19]([CH2:35][C:36]1[CH:37]=[CH:38][C:39]([CH2:42][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]3[CH2:10][CH:9]3[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:7]=2)=[CH:40][CH:41]=1)[C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:29][CH:30]=2)[N:24]=1

참가 물질

7

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23157500{4-[((3-Methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]phenyl}methanolHCID 59364069Methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate

생성물 1

HCID 59364067Methyl 2-[4-({4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzyl}oxy)phenyl]cyclopropanecarboxylate수율 46.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8058Hexane용매

실험 절차

A solution of methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.152 g, 0.790 mmol), {4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3- thiazol-2-yl}amino)methyl]phenyl}methanol (0.312 g, 0.718 mmol) and tributylphosphine (0.291 g, 1.44 mmol) in toluene (15 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (0.363 g, 1.44 mmol) was added, and the mixture was stirred at room temperature for 60 hr. Hexane (15 mL) was added to the reaction mixture, and the precipitated insoluble material was filtrated. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70) to give the title compound (0.202 g, yield 42%) as a colorless oil.

후처리

  1. filtrationthe precipitated insoluble material was filtrated
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70)

출처 및 근거

ORD 기록
ord-d231ac9ac7164a6595a53f67d540ef30
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153694B2

반응 노트

불러오는 중…