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Methanol → 6-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenyl}-nicotinic acid

HRID 1095906
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인쇄 미리보기

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HRID 1095906 반응식
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:30])[C:17]([OH:29])([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([CH3:28])[CH:23]=3)[C:18]([F:21])([F:20])[F:19])=[C:12]([Cl:31])[CH:11]=2)=[N:6][CH:5]=1.[Li+].[OH-].CO>C1COCC1>[Cl:31][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:32])=[O:2])=[CH:5][N:6]=2)[CH:15]=[CH:14][C:13]=1[CH:16]([CH3:30])[C:17]([OH:29])([C:22]1[CH:27]=[CH:26][N:25]=[C:24]([CH3:28])[CH:23]=1)[C:18]([F:20])([F:19])[F:21]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 666991666-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenyl}-nicotinic acid methyl ester

생성물 1

HCID 595085726-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenyl}-nicotinic acid수율 98.4%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To 6-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenyl}-nicotinic acid methyl ester (22 mg) aqueous 1N LiOH (5 ml), MeOH (2.5 ml) and THF (5 ml) were added. The resulting solution was stirred for 2 h at room temperature. Volatile solvents were removed in vacuo. The residual aqueous solution was diluted with water (10 ml) and washed with DCM (10 ml), then acidified to pH 6 with 1 N aqueous HCl and extracted with EtOAc. The combined EtOAc layers were dried over Na2SO4 and concentrated to give the title compound (21 mg) as a yellow oil. MS (m/e)=451.0 [M+H+].

후처리

  1. customVolatile solvents were removed in vacuo
  2. additionThe residual aqueous solution was diluted with water (10 ml)
  3. washwashed with DCM (10 ml)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined EtOAc layers were dried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f079cf7883794a5bb70df63c6ab0c3f0
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08138189B2

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