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 24006노트

반응식

HRID 24006 반응식
[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]

참가 물질

7

반응물 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, 화합물

생성물 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 ester수율 493.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d05016fac233425dad76ccec7fcdfbad
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855722B2

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