Phosphate → 2-[(2-{(1R,2R)-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxocyclopentyl}ethyl)sulfanyl]-1,3-thiazole-4-carboxylic acid

HRID 1888302ノート

反応式

HRID 1888302 の反応式
[OH:1][C@@H:2]([CH2:24][C@@H:25]([CH3:30])[CH2:26][CH2:27][CH2:28][CH3:29])/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[C@@H:6]1[CH2:11][CH2:12][S:13][C:14]1[S:15][CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[N:18]=1.P([O-])([O-])([O-])=O>CS(C)=O.C(OCC)(=O)C>[OH:1][C@@H:2]([CH2:24][C@@H:25]([CH3:30])[CH2:26][CH2:27][CH2:28][CH3:29])/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[C@@H:6]1[CH2:11][CH2:12][S:13][C:14]1[S:15][CH:16]=[C:17]([C:19]([OH:21])=[O:20])[N:18]=1

参加物

5

反応物 2

HCID 1061PhosphateHCID 66858273ethyl 2-[(2-{(1R,2R)-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxocyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylate

生成物 1

HCID 112011132-[(2-{(1R,2R)-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxocyclopentyl}ethyl)sulfanyl]-1,3-thiazole-4-carboxylic acid収率 66.1%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of the compound 29 (142 mg) in dimethylsulfoxide (7.00 mL)/phosphate buffer (7.00 mL) was added esterase from porcine liver (0.850 mL) and the solution was stirred at room temperature for 4 hours. The reaction solution was diluted with ethyl acetate and washed with an aqueous saturated ammonium sulfate solution, 1N hydrochloric acid, water and brine. The reaction solution was dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate), to give the title compound (88.0 mg) having the following physical data.

後処理

  1. washwashed with an aqueous saturated ammonium sulfate solution, 1N hydrochloric acid, water and brine
  2. dry with materialThe reaction solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate)

出典と根拠

ORDレコード
ord-918df66f60d9407c95c0eaa312e929d2
出典データセット
uspto-grants-2013_08
特許番号
US08501793B2

反応ノート

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