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Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate → t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonyl-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoate

HRID 1198968
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HRID 1198968 반응식
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH:35]=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.[C:37]([CH2:42][CH:43]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:39][CH2:40][CH3:41])=[O:38]>O1CCOCC1>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH:35]=[C:42]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH3:43])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[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 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoateHCID 15013776t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-formylindol-1-ylmethyl]3-methoxybenzoate

생성물 1

HCID 53856301t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonyl-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoate수율 100.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-formylindol-1-ylmethyl]3-methoxybenzoate (Example 1, part(f)) (2.8 g) and (carbethoxyethylidene)triphenylphosphorane (4.6 g) in dioxane (29 ml) was heated at reflux for 18 hours. The solvent was evaporated. The resultant residue was purified by flash chromatography on silica gel (192 ml), eluting with 1:4 ethyl acetate:hexane to give t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonyl-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoate (3.3 g, 100%) as a light yellow solid; mp 118°-120°; NMR (80 MHz, CDCl3) 2.15(d, 3H, CCH3), 3.40(dd, 2H, NHCH2), 5.42(s, 2H, NCH2), 6.22(br t, 1H, NH), 6.78(d, 1H, Ar).

후처리

  1. temperatureat reflux for 18 hours
  2. customThe solvent was evaporated
  3. customThe resultant residue was purified by flash chromatography on silica gel (192 ml)
  4. washeluting with 1:4 ethyl acetate

출처 및 근거

ORD 기록
ord-2bc86316e88e4a7b8a84a7484aef4554
출처 데이터셋
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04898863

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