Tributylphosphine → Ethyl 3-{[(4-{[{5-[(6-chloropyridin-3-yl)methoxy]-3-methyl-1-benzofuran-2-yl}(cyclohexyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate

HRID 2091367ノート

反応式

HRID 2091367 の反応式
[CH:1]1([CH:7]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([N:28]([CH3:36])[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.[Cl:37][C:38]1[N:43]=[CH:42][C:41]([CH2:44]O)=[CH:40][CH:39]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[Cl:37][C:38]1[N:43]=[CH:42][C:41]([CH2:44][O:18][C:15]2[CH:16]=[CH:17][C:10]3[O:9][C:8]([CH:7]([NH:19][C:20]4[CH:21]=[CH:22][C:23]([C:26]([N:28]([CH3:36])[CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[CH:24][CH:25]=4)[CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[C:12]([CH3:13])[C:11]=3[CH:14]=2)=[CH:40][CH:39]=1

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 177161(6-Chloropyridin-3-yl)methanolHCID 66777718HCID 66777718、化合物

生成物 1

HCID 86662756Ethyl 3-{[(4-{[{5-[(6-chloropyridin-3-yl)methoxy]-3-methyl-1-benzofuran-2-yl}(cyclohexyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate収率 66%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Ethyl 3-{[(4-{[cyclohexyl(5-hydroxy-3-methyl-1-benzofuran-2-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate (0.39 g) synthesized in Example A155(1) was dissolved in tetrahydrofuran (5 mL), 6-chloro-3-pyridinemethanol (140 mg), tributylphosphine (0.35 mL) and 1,1′-(azodicarbonyl)dipiperidine (0.36 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 (0.32 g, 66%) as a yellow oil.

後処理

  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)

出典と根拠

ORDレコード
ord-bd7506a394c5455384c2f85170c60652
出典データセット
uspto-grants-2013_05
特許番号
US08436043B2

反応ノート

読み込み中…