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Potassium Carbonate → (7R,8R,9R)-3,9-Diphenyl-8-hydroxy-7-(2-methoxyethoxy)-2-methyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 723391
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HRID 723391 반응식
C([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:23])=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([O:24][CH2:25][CH2:26][O:27][CH3:28])[C@H:6]([O:29]C(=O)C(C)(C)C)[C@H:5]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>NC(O)C>[C:17]1([C:16]2[N:11]3[CH:10]=[CH:9][C:8]4[C@@H:7]([O:24][CH2:25][CH2:26][O:27][CH3:28])[C@H:6]([OH:29])[C@@H:5]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[NH:4][C:13]=4[C:12]3=[N:14][C:15]=2[CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 69586312(7R,8R,9R)-10-acetyl-3,9-diphenyl-7-(2-methoxyethoxy)-2-methyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

생성물 1

HCID 11304956(7R,8R,9R)-3,9-Diphenyl-8-hydroxy-7-(2-methoxyethoxy)-2-methyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

시약·촉매·용매 1

HCID 522583Acetaldehyde ammonia용매

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온도
60 °C

실험 절차

A suspension of 1.14 g (2.05 mmol) of (7R,8R,9R)-10-acetyl-3,9-diphenyl-7-(2-methoxyethoxy)-2-methyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine and 2.28 g (16.5 mmol) potassium carbonate in aminoethanol is stirred at 60° C. for 4 h. The reaction is quenched by adding of saturated aqueous ammonium chloride solution. Subsequently the mixture is extracted twice with ethyl acetate. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (diethyl ether/petrol ether: 7/3) to give 0.52 g (1.21 mmol/60%) of the title compound as a colourless solid with a melting point of 190–192° C. (diethyl ether).

후처리

  1. customThe reaction is quenched
  2. additionby adding of saturated aqueous ammonium chloride solution
  3. extractionSubsequently the mixture is extracted twice with ethyl acetate
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customThe crude product is purified by column chromatography (diethyl ether/petrol ether: 7/3)

출처 및 근거

ORD 기록
ord-6abd21351a764ff39d10a9b922d64dda
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07141567B2

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