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Lithium Hydroxide → Pexopiprant

HRID 2266521
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HRID 2266521 반응식
C[O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:30])[F:29])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:31])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH2:17][CH3:18])[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)=[C:8]2[O:27][CH:28]([F:30])[F:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 68780330HCID 68780330, 화합물

생성물 1

HCID 16038335Pexopiprant

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of [8-chloro-3-(4-chlorobenzyl)-4-difluoromethoxy-2-ethylquinolin-5-yloxy]acetic acid methyl ester (0.017 g), tetrahydrofuran (3.0 mL) and 1.0 M aqueous lithium hydroxide solution (0.20 mL) was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the residue diluted with water. The pH of the resulting mixture was adjusted to 5 by the addition of sodium dihydrogenphosphate and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. Purification of the residue by preparative reverse-phase HPLC using a gradient of acetonitrile in water (30% to 95% of organic modifier) gave title compound, 0.010 g.

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with water
  3. additionThe pH of the resulting mixture was adjusted to 5 by the addition of sodium dihydrogenphosphate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. customthe solvent removed under reduced pressure
  7. customPurification of the residue by preparative reverse-phase

출처 및 근거

ORD 기록
ord-4cce6ccec8c7432a96a2d3f98d4f8a31
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07858640B2

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