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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
ノート
印刷プレビュー

反応式

HRID 1198968 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2bc86316e88e4a7b8a84a7484aef4554
出典データセット
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04898863

反応ノート

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