Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylvinyl)indol-1-ylmethyl]-3-methoxybenzoate

HRID 1198959노트

반응식

HRID 1198959 반응식
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14](C=O)=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:11]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(=[CH:56][C:57]([O:59][CH3:60])=[O:58])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOC[CH2:62]1>>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH:62]=[CH:56][C:57]([O:59][CH3:60])=[O:58])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:11]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

4

반응물 3

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 312751,4-DioxaneHCID 15013776t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-formylindol-1-ylmethyl]3-methoxybenzoate

생성물 1

HCID 54500983t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylvinyl)indol-1-ylmethyl]-3-methoxybenzoate수율 84%

실험 절차

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-formylindol-1-ylmethyl]-3-methoxybenzoate (1.2 g) and methyl (triphenylphosphoranylidene)acetate (1.8 g) in dioxane (12 ml) was heated at reflux for 48 hours. The solvent was evaporated. The resultant residue was purified by flash chromatography on silica gel (600 ml), eluting with 3:7 ethyl acetate:hexane, to give t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylvinyl)indol-1-ylmethyl]-3-methoxybenzoate (1.1 g, 84%) as a yellow solid; mp 163°-164°.

후처리

  1. temperatureat reflux for 48 hours
  2. customThe solvent was evaporated
  3. customThe resultant residue was purified by flash chromatography on silica gel (600 ml)
  4. washeluting with 3:7 ethyl acetate

출처 및 근거

ORD 기록
ord-4a9070751ca749af8a796669187dc9c4
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04898863

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