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 1888302노트

반응식

HRID 1888302 반응식
[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

참가 물질

5

반응물 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

생성물 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 acid수율 66.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-918df66f60d9407c95c0eaa312e929d2
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501793B2

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