Tetrahydrofuran → 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 4-((E)-2-carboxy-vinyl)-phenyl ester

HRID 1827011노트

반응식

HRID 1827011 반응식
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1/[CH:8]=[C:9]1\[C:10](=[O:25])[N:11]([C:18](N2C=CN=C2)=[O:19])[C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2.[C:26]([OH:36])(=[O:35])[CH:27]=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1C[O:40]CC1>C(N(CC)CC)C>[C:26](/[CH:27]=[CH:28]/[C:29]1[CH:30]=[CH:31][C:32]([O:40][C:18]([N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)/[C:9](=[CH:8]/[C:3]3[NH:4][C:5]([CH3:7])=[CH:6][C:2]=3[CH3:1])/[C:10]2=[O:25])=[O:19])=[CH:33][CH:34]=1)([OH:36])=[O:35]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 87842-Propenoic acid, 3-phenyl-HCID 601112313-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indol-2-one

생성물 1

HCID 601112193-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 4-((E)-2-carboxy-vinyl)-phenyl ester수율 16%

시약·촉매·용매 1

HCID 8471Triethylamine촉매

반응 조건

온도
60 °C

실험 절차

A reaction mixture of of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indol-2-one (165 mg, 0.5 mmol), cinnamic acid (85 mg, 0.5 mmol), and 2 drops of triethylamine in 3 mL of THF was stirred at 60° C. for 5 h and room temperature overnight and filtered. The solid was then washed with ethyl acetate and 1 N aqueous hydrogen chloride solution. The filtrate was concentrated and the residue was partitioned between ethyl acetate and water-acetic acid. The organic layer was washed with diluted sodium hydroxide solution, dried over magnesium sulfate, and concentrated. The resultant residue was suspended in warm ethyl acetate and filtered. The combined solid was then dried in a vacuum oven overnight to afford 35 mg (16%) of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 4-((E)-2-carboxy-vinyl)-phenyl ester. 1H NMR (400 MHz, DMSO-d6) δ 12.55 (s, 1H, NH-1′), 12.41 (s, br, 1H, COOH), 7.91–7.94 (m, 1H), 7.82–7.85 (m, 3H), 7.71 (s, 1H, H-vinyl), 7.65 (d, J=6.02 Hz, 1H), 7.44 (d, J=8.99 Hz, 1H), 7.24–7.26 (m, 2H), 6.57 (d, J=6.02 Hz, 1H), 6.15 (d, J=2.35 Hz, 1H, H-4′), 2.39 (s, 3H, CH3), and 2.37 (s, 3H, CH3).

후처리

  1. filtrationfiltered
  2. washThe solid was then washed with ethyl acetate and 1 N aqueous hydrogen chloride solution
  3. concentrationThe filtrate was concentrated
  4. customthe residue was partitioned between ethyl acetate and water-acetic acid
  5. washThe organic layer was washed with diluted sodium hydroxide solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. filtrationfiltered
  9. customThe combined solid was then dried in a vacuum oven overnight

출처 및 근거

ORD 기록
ord-61baca3cd1084c45a25ebf627835b59c
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053114B2

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