Lithium hydroxide, monohydrate → (Z)-3-(Furan-3-yl)-2-methoxy-6-((2-(3-(piperidin-1-yl)prop-1-enyl)benzenesulfonyl)methyl)benzoic acid

HRID 2177683노트

반응식

HRID 2177683 반응식
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([O:35][CH3:36])=[C:8]([C:13]([CH2:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3/[CH:26]=[CH:27]\[CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)(=[O:19])=[O:18])=[CH:14][CH:15]=2)[C:9]([O:11]C)=[O:10])=[CH:2]1.O.[OH-].[Li+]>O.O1CCOCC1>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([O:35][CH3:36])=[C:8]([C:13]([CH2:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3/[CH:26]=[CH:27]\[CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)(=[O:19])=[O:18])=[CH:14][CH:15]=2)[C:9]([OH:11])=[O:10])=[CH:2]1

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 69915028(Z)-Methyl 3-(furan-3-yl)-2-methoxy-6-((2-(3-(piperidin-1-yl)prop-1-enyl)benzenesulfonyl)methyl)benzoate2회

생성물 1

HCID 52913530(Z)-3-(Furan-3-yl)-2-methoxy-6-((2-(3-(piperidin-1-yl)prop-1-enyl)benzenesulfonyl)methyl)benzoic acid

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

반응 조건

온도
65 °C

실험 절차

(Z)-Methyl 3-(furan-3-yl)-2-methoxy-6-((2-(3-(piperidin-1-yl)prop-1-enyl)benzenesulfonyl)methyl)benzoate (Intermediate 198, 0.069 g) was added to a solution of lithium hydroxide monohydrate (0.051 g) in water (0.7 ml) and dioxane (3 ml) and the resultant mixture was stirred and heated at 65° C. for 4 days. After cooling, the mixture was diluted with water and washed with diethyl ether. The aqueous layer was acidified with 1M HCl and extracted with ethyl acetate, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by HPLC (C6 phenyl column) eluting with 1:1 methanol:water containing 0.1% formic acid to give (Z)-3-(Furan-3-yl)-2-methoxy-6-((2-(3-(piperidin-1-yl)prop-1-enyl)benzenesulfonyl)methyl)benzoic acid as a white solid.

후처리

  1. temperatureAfter cooling
  2. washwashed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by HPLC (C6 phenyl column)
  9. washeluting with 1:1 methanol

출처 및 근거

ORD 기록
ord-ae7889dae9944bf8891f8ccc192a293e
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

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