Pyridine → HCID 178496221, 화합물

HRID 53463노트

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HRID 53463 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

HCID 178496221HCID 178496221, 화합물수율 93.9%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bd5674891c5140d7b096a8298f271e93
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618970

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