Lithium Hydroxide → 3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid

HRID 1935216

반응식

HRID 1935216 반응식
C[O:2][C:3](=[O:26])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[CH:20]3)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][CH:21]=[CH:20]4)=[CH:13][CH:12]=2)[C:3]([OH:26])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 674852183-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid methyl ester

생성물 1

HCID 224679073-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

A solution of 3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid methyl ester (310 mg, 0.89 mmol) in tetrahydrofuran (2 mL) was treated with a 0.8M aqueous lithium hydroxide solution (1.45 mL, 1.16 mmol). The resulting reaction mixture was stirred at 25° C. for 39 h and then heated at 80° C. for 4 h. The reaction mixture was then allowed to cool to 25° C. where it was stirred for 3 d. The reaction mixture was then concentrated in vacuo to remove tetrahydrofuran. The resulting aqueous layer was extracted with methylene chloride (2×40 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid (170 mg, 58%) as a pale yellow foam: mp 62-65° C.; FAB-HRMS m/e calcd for C22H23NO2 (M+H)+ 333.1729, found 333.1731.

후처리

  1. customThe resulting reaction mixture
  2. temperatureheated at 80° C. for 4 h
  3. temperatureto cool to 25° C. where it
  4. stirringwas stirred for 3 d
  5. concentrationThe reaction mixture was then concentrated in vacuo
  6. customto remove tetrahydrofuran
  7. extractionThe resulting aqueous layer was extracted with methylene chloride (2×40 mL)
  8. dry with materialThe combined organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0ff4a4bc9fae4468a1e27333cc3920d2
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384220B2

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