Tetrahydrofuran → [6-chloro-2-[(5,6,7,8-tetrahydroisoquinolin-3-yl)carbonyl]-1H-indol-3-yl]acetic acid

HRID 380562노트

반응식

HRID 380562 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:23][C:24]([O:26]C)=[O:25])=[C:7]([C:11]([C:13]3[N:14]=[CH:15][C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=4[CH:22]=3)=[O:12])[NH:8]2)=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:23][C:24]([OH:26])=[O:25])=[C:7]([C:11]([C:13]3[N:14]=[CH:15][C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=4[CH:22]=3)=[O:12])[NH:8]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 9908023methyl [6-chloro-2-[(5,6,7,8-tetrahydroisoquinolin-3-yl)carbonyl]-1H-indol-3-yl]acetate

생성물 1

HCID 9864100[6-chloro-2-[(5,6,7,8-tetrahydroisoquinolin-3-yl)carbonyl]-1H-indol-3-yl]acetic acid수율 60.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a mixture of methyl [6-chloro-2-[(5,6,7,8-tetrahydroisoquinolin-3-yl)carbonyl]-1H-indol-3-yl]acetate (Example 1) in MeOH (20 ml)-THF (20 ml) was added 2N aqueous NaOH (0.6 ml, 1.2 mmol) at room temperature and the resulting mixture was heated at reflux temperature for 8 h. The mixture was cooled and concentrated. The residue was dissolved in water (20 ml) and washed with diethyl ether (20 ml×3). The aqueous layer was acidified with 2N aqueous HCl and extracted with ethyl acetate (40 ml×3). The combined organic layers were dried (MgSO4) and concentrated. The residue was recrystallized from ethyl acetate to afford 23.3 mg (60.7%) of the title compound as yellow solids.

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux temperature for 8 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in water (20 ml)
  6. washwashed with diethyl ether (20 ml×3)
  7. extractionextracted with ethyl acetate (40 ml×3)
  8. dry with materialThe combined organic layers were dried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-aebf1b63a2d043f0a7122a7e06db3749
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303628B1

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