Sodium Hydroxide → 4-(3-(2-(3-Hydroxy-4-phenylbutyl)-5-oxopyrrolidin-1-yl)propyl)benzoic acid

HRID 458966노트

반응식

HRID 458966 반응식
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH:21]([OH:29])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[OH:29][CH:21]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:20][CH2:19][CH:14]1[CH2:15][CH2:16][C:17](=[O:18])[N:13]1[CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:30])=[O:2])=[CH:9][CH:8]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 129700864-{3-[2-(3-Hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-propyl}-benzoic acid methyl ester

생성물 1

HCID 113268964-(3-(2-(3-Hydroxy-4-phenylbutyl)-5-oxopyrrolidin-1-yl)propyl)benzoic acid수율 92.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 4-{3-[2-(3-hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-propyl}-benzoic acid methyl ester (2.28 g, 5.57 mmol) in MeOH (20 mL) was added 2N NaOH (5 mL). The reaction mixture was stirred at room temperature for 20 h and was heated under reflux for 3 h. The volatiles were removed in vacuo and the residue was diluted with CH2Cl2 and 1N HCl. The aqueous solution was extracted with CH2Cl2 (2×) and the combined organic extracts were washed with brine. The organic solution was dried (MgSO4), filtered and concentrated to yield the title compound (2.03 g). 1H NMR (CDCl3) δ7.98 (d, 2H), 7.34–7.18 (m, 7H), 3.80 (m, 1H), 3.67 (m, 1H), 3.58 (m, 1H), 2.97 (m, 1H), 2.81 (m, 1H), 2.68 (m, 3H), 2.45–2.27 (m, 2H), 2.13–1.30 (m, 9H); MS 396.3 (M+1), 394.2 (M−1).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customThe volatiles were removed in vacuo
  4. additionthe residue was diluted with CH2Cl2 and 1N HCl
  5. extractionThe aqueous solution was extracted with CH2Cl2 (2×)
  6. washthe combined organic extracts were washed with brine
  7. dry with materialThe organic solution was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-60c24956149b49a49692b88f3e7c7ab9
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192979B2

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