Methanol → 7-(2-{1-[1-(3-Benzyloxy-phenyl)-2-ethoxycarbonyl-ethyl]-1H-indol-5-yloxy}-ethyl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

HRID 24006ノート

反応式

HRID 24006 の反応式
[I-].[Sm+2].[I-].[C:4]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][CH2:22][O:23][C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[N:29]([C:33]([C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH2:47][C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=5)[CH:41]=3)=[CH:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:28]=[CH:27]4)[N:19]=2)[CH2:14][CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].CN(C)P(N(C)C)(N(C)C)=O.CO.[Cl-].[NH4+]>C(O)C>[C:4]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][CH2:22][O:23][C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[N:29]([CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH2:47][C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=5)[CH:41]=3)[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:28]=[CH:27]4)[N:19]=2)[CH2:14][CH2:13][CH2:12]1)=[O:10])([CH3:5])([CH3:6])[CH3:7]

参加物

7

反応物 5

HCID 887MethanolHCID 12679HexamethylphosphoramideHCID 25517Ammonium ChlorideHCID 668211417-(2-{1-[1-(3-benzyloxy-phenyl)-2-ethoxycarbonyl-vinyl]-1H-indol-5-yloxy}-ethyl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl esterHCID 178506586HCID 178506586、化合物

生成物 1

HCID 668214097-(2-{1-[1-(3-Benzyloxy-phenyl)-2-ethoxycarbonyl-ethyl]-1H-indol-5-yloxy}-ethyl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester収率 493.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Samarium(II) iodide [0.1 M in THF] (14.8 mL, 14.8 mmol) was added to a solution of 7-(2-{1-[1-(3-benzyloxy-phenyl)-2-ethoxycarbonyl-vinyl]-1H-indol-5-yloxy}-ethyl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (0.10 g, 0.15 mmol), hexamethylphosphoramide (0.39 mL, 2.22 mmol) and either ethanol or methanol (10 equivalents) and stirred at room temperature overnight. Saturated ammonium chloride (20 mL) was added to the reaction and the crude product was extracted with ethyl acetate (3×20 mL). The crude mixture was then purified via column chromatography in silica gel (20% ethyl acetate in hexane) to give the title compound (0.50 g, 50% yield). 1H NMR (CDCl3) δ 7.28-7.22 (m, 5H), 7.13 (m, 4H), 7.08 (d, 1H, J=3.2 Hz), 6.86 (m, 1H), 6.79-6.69 (m, 4H), 6.35 (d, 1H, J=3.2 Hz), 5.99 (t, 1H, J=7.5 Hz), 4.98 (s, 2H), 4.29 (t, 2H, J=6.9 Hz), 3.96 (q, 2H, J=7.1 Hz), 3.68 (m, 2H), 3.18-3.10 (m, 4H), 2.66 (m, 2H), 1.85 (m, 2H), 1.45 (s, 9H), 1.01 (t, 3H, J=7.1 Hz).

後処理

  1. extractionthe crude product was extracted with ethyl acetate (3×20 mL)
  2. customThe crude mixture was then purified via column chromatography in silica gel (20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-d05016fac233425dad76ccec7fcdfbad
出典データセット
uspto-grants-2005_02
特許番号
US06855722B2

反応ノート

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