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Methanol → 4-[1-(4-Fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid

HRID 889039
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HRID 889039 반응식
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]2[CH2:16][C:15](=[O:17])[N:14]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:13]2)=[CH:6][CH:5]=1.CO.O.O[Li].O>C1COCC1>[F:24][C:21]1[CH:20]=[CH:19][C:18]([N:14]2[C:15](=[O:17])[CH2:16][CH:12]([CH2:11][O:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[CH:5][CH:6]=3)[CH2:13]2)=[CH:23][CH:22]=1
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참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 117249774-[1-(4-Fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid methyl ester

생성물 1

HCID 104717594-[1-(4-Fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid수율 96.8%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a stirred solution of 4-[1-(4-fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid methyl ester obtained in step 1 (0.14 g, 0.408 mmol) in THF:MeOH:H2O (6 mL, 2:1:3), LiOH.H2O was added at 20-25° C. The reaction mixture was stirred for 16 hours at that temperature. The solvents were removed under reduced pressure and the residue was diluted with water (10 ml). The aqueous layer was washed with DCM, acidified with 2% HCl. The acidified mixture was extracted with ethyl acetate, washed with brine, dried over Na2SO4. The organic layer was evaporated under reduced pressure to obtain 4-[1-(4-fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid (0.130 g, quantitative) as a white solid.

후처리

  1. customThe solvents were removed under reduced pressure
  2. additionthe residue was diluted with water (10 ml)
  3. washThe aqueous layer was washed with DCM
  4. extractionThe acidified mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe organic layer was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-91a2a5b82f5f4a838bd20c00f1b9b1f3
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08252797B2

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