Pyridine → HCID 178496221、化合物

HRID 53463ノート

反応式

HRID 53463 の反応式
[C:1]([O:5][C:6](/[C:8](/[CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:9]/[C:10]1([C:15](O)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.S(Cl)(Cl)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:45][C@@H:46]1[CH2:51][CH2:50][C@H:49]([C:52]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[O:53])[CH2:48][CH2:47]1.C(N(CC)CC)C>C(OCC)(=O)C.CN(C)C=O.O>[C:1]([O:5][C:6](/[C:8](/[CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:9]/[C:10]1([C:15]([NH:45][C@@H:46]2[CH2:51][CH2:50][C@H:49]([C:52]([O:54][CH2:55][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)=[O:53])[CH2:48][CH2:47]2)=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

9

反応物 5

HCID 1049PyridineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 11069968(E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acidHCID 178427656HCID 178427656、化合物

生成物 1

HCID 178496221HCID 178496221、化合物収率 93.9%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of (E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid (1.0 g, 3.04 mmol) in ethyl acetate (10.6 mL) under a nitrogen atmosphere at room temperature was added dimethylformamide (1 drop), pyridine (0.49 mL, 6.08 mmol) and thionyl chloride (0.28 mL, 3.95 mmol) and the mixture stirred at room temperature for 40 minutes. Benzyl cis-4-amino-1-cyclohexanecarboxylate p-toluenesulphonate (1.29 g, 3.19 mmol) was added at room temperature followed by triethylamine (1.27 mL, 9.12 mmol) and the mixture stirred at room temperature for 3 hours. The reaction mixture was diluted with distilled water (50 mL) and ethyl acetate (50 mL) and the layers separated. The ethyl acetate layer was washed with distilled water (2×50 mL), 1.0M aqueous hydrochloric acid solution (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a brown oil (1.552 g). The crude product was purified by chromatography on silica by elution with hexane/ethyl acetate (1:1) to give, after combination and evaporation of appropriate fractions, the title compound as an oil (1.07 g, 65%).

後処理

  1. stirringthe mixture stirred at room temperature for 3 hours
  2. customthe layers separated
  3. washThe ethyl acetate layer was washed with distilled water (2×50 mL), 1.0M aqueous hydrochloric acid solution (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-bd5674891c5140d7b096a8298f271e93
出典データセット
uspto-grants-1997_04
特許番号
US05618970

反応ノート

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