Lithium Hydroxide → [8-Chloro-4-difluoromethoxy-2-ethyl-3-(4-isobutyrylbenzyl)quinolin-5-yloxy]acetic acid

HRID 1922107노트

반응식

HRID 1922107 반응식
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:31][CH:32]([F:34])[F:33])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1.O>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:35])=[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]([C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[CH:24][CH:25]=1)=[C:8]2[O:31][CH:32]([F:34])[F:33]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 67458281[8-Chloro-4-difluoromethoxy-2-ethyl-3-(4-isobutyrylbenzyl)quinolin-5-yloxy]acetic acid methyl ester

생성물 1

HCID 25096080[8-Chloro-4-difluoromethoxy-2-ethyl-3-(4-isobutyrylbenzyl)quinolin-5-yloxy]acetic acid수율 84.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of [8-chloro-4-difluoromethoxy-2-ethyl-3-(4-isobutyrylbenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.22 g) in tetrahydrofuran (5.0 mL) and water (1.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.86 mL), and the resulting mixture was stirred at room temperature for 2 hours. The mixture was concentrated to low bulk under reduced pressure, and the pH adjusted to 4-5 by the addition of 1.0 M aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate, and the combined extracts were dried over magnesium sulfate and then concentrated under reduced pressure. Purification of the residue by preparative reverse-phase HPLC gave title compound (0.18 g).

후처리

  1. concentrationThe mixture was concentrated to low bulk under reduced pressure
  2. additionthe pH adjusted to 4-5 by the addition of 1.0 M aqueous hydrochloric acid solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-d261d75a2ad7449581cdea7e11eac88e
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173812B2

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