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Methanol → (5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-fluoro-phenyl}-pyridin-3-yl)-acetic acid

HRID 554640
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HRID 554640 반응식
C([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[CH2:19][N:20]([C:23]([CH:25]2[CH2:27][CH2:26]2)=[O:24])[CH2:21][CH3:22])[CH:11]=1)C.[Li+].[OH-].CO>C1COCC1>[CH:25]1([C:23]([N:20]([CH2:19][C:13]2[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=2[C:10]2[CH:11]=[C:6]([CH2:5][C:4]([OH:28])=[O:3])[CH:7]=[N:8][CH:9]=2)[CH2:21][CH3:22])=[O:24])[CH2:27][CH2:26]1
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참가 물질

5

반응물 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 58565012(5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4fluoro-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

생성물 1

HCID 45138779(5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-fluoro-phenyl}-pyridin-3-yl)-acetic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
35 °C

실험 절차

(5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-fluoro-phenyl}-pyridin-3-yl)-acetic acid ethyl ester (0.202 g, 0.53 mmol) was dissolved in THF (5.25 mL) and treated with 1N aqueous LiOH (2.63 mL, 2.63 mmol) and a small amount of MeOH. The reaction was stirred at 35° C. for 30 minutes. The mixture was concentrated, and the residue was diluted with H2O and washed with EtOAc. The aqueous layer was acidified with 1N aqueous HCl to pH 6 and extracted with EtOAc, and the combined organic layers were washed with H2O and brine, and then dried over Na2SO4, filtered, and concentrated to give Compound 23.

후처리

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with H2O
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. washthe combined organic layers were washed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5f191085416e444aa4a1e0db500acab5
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08049015B2

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