Water → ethyl 2-[(2-{(1R,2R)-2-[(1E)-5-cyclohexyl-4-hydroxy-4-methyl-1-pentenyl]-5-oxocyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylate

HRID 1888313ノート

反応式

HRID 1888313 の反応式
[CH:1]1([CH2:7][C:8]([OH:32])([CH3:31])[CH2:9]/[CH:10]=[CH:11]/[C@H:12]2[CH2:16][CH2:15][C@H:14]([OH:17])[C@@H:13]2[CH2:18][CH2:19][S:20][C:21]2[S:22][CH:23]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OCC)(=O)C.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH:1]1([CH2:7][C:8]([OH:32])([CH3:31])[CH2:9]/[CH:10]=[CH:11]/[C@H:12]2[CH2:16][CH2:15][C:14](=[O:17])[C@@H:13]2[CH2:18][CH2:19][S:20][C:21]2[S:22][CH:23]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:25]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 68771064ethyl 2-[(2-{(1R,2R,5S)-2-[(1E)-5-cyclohexyl-4-hydroxy-4-methyl-1-pentenyl]-5-hydroxycyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxyl ate

生成物 1

HCID 66858314ethyl 2-[(2-{(1R,2R)-2-[(1E)-5-cyclohexyl-4-hydroxy-4-methyl-1-pentenyl]-5-oxocyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylate収率 63.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of the compound 51 (242 mg) in dimethylsulfoxide (2.0 mL)/ethyl acetate (4.0 mL) were added diisopropylethylamine (0.70 mL) and sulfur trioxide-pyridine complex (320 mg) at 10° C. and the solution was stirred for 30 minutes. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed 1N hydrochloric acid, water and brine, anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=7:3) to give the title compound (154 mg) having the following physical data.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed 1N hydrochloric acid, water and brine, anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=7:3)

出典と根拠

ORDレコード
ord-1df9d3c584214626b3140450fe33a498
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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