Tributylphosphine → Ethyl 3-[({4-[(cyclohexyl{5-[(2-fluoropyridin-4-yl)methoxy]-3-methyl-1-benzofuran-2-yl}methyl)amino]phenyl}carbonyl)amino]propanoate

HRID 2091362노트

반응식

HRID 2091362 반응식
[CH:1]1([CH:7]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([NH:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[CH:22][CH:21]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:36][C:37]1[CH:42]=[C:41]([CH2:43]O)[CH:40]=[CH:39][N:38]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH:1]1([CH:7]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([NH:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[CH:24][CH:25]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([O:18][CH2:43][C:41]4[CH:40]=[CH:39][N:38]=[C:37]([F:36])[CH:42]=4)=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 11332468(2-Fluoropyridin-4-yl)methanolHCID 66778243Ethyl 3-{[(4-{[cyclohexyl(5-hydroxy-3-methyl-1-benzofuran-2-yl)methyl]amino}phenyl)carbonyl]amino}propanoate2회

생성물 1

HCID 66777071Ethyl 3-[({4-[(cyclohexyl{5-[(2-fluoropyridin-4-yl)methoxy]-3-methyl-1-benzofuran-2-yl}methyl)amino]phenyl}carbonyl)amino]propanoate수율 54%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl 3-{[(4-{[cyclohexyl(5-hydroxy-3-methyl-1-benzofuran-2-yl)methyl]amino}phenyl)carbonyl]amino}propanoate (0.36 g) synthesized in the above-mentioned (1) was dissolved in tetrahydrofuran (5 mL), and 2-fluoro-4-pyridinemethanol (114 mg), tributylphosphine (0.35 mL) and 1,1′-(azodicarbonyl)dipiperidine (0.34 g) were added to the solution under ice-cooling. The ice bath was removed, the reaction mixture was stirred at room temperature for 12 hr, then hexane (5 mL) was added to the mixture, and the precipitate was filtered off through celite. Water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (0.23 g, 54%) as a yellow oil.

후처리

  1. temperaturecooling
  2. customThe ice bath was removed
  3. additionhexane (5 mL) was added to the mixture
  4. filtrationthe precipitate was filtered off through celite
  5. additionWater was added to the filtrate
  6. extractionthe mixture was extracted with ethyl acetate
  7. concentrationThe extract was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

출처 및 근거

ORD 기록
ord-1ae98563a0804a469f27c8b37ea34c34
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

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