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

HRID 2177683ノート

反応式

HRID 2177683 の反応式
[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

参加物

5

反応物 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)benzoate2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
65 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-ae7889dae9944bf8891f8ccc192a293e
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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