Potassium ethanethioate → (3S,5S)-3-Acetylthio-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine

HRID 568267ノート

反応式

HRID 568267 の反応式
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[CH2:6]([O:9][C:10]([N:12]1[C@H:16]([CH:17]([OH:26])[C:18]2[N:19]3[CH:25]=[N:24][CH:23]=[C:20]3[S:21][CH:22]=2)[CH2:15][C@@H:14](OS(C)(=O)=O)[CH2:13]1)=[O:11])[CH:7]=[CH2:8]>CN(C=O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([S:3][C@H:14]1[CH2:15][C@@H:16]([CH:17]([OH:26])[C:18]2[N:19]3[CH:25]=[N:24][CH:23]=[C:20]3[S:21][CH:22]=2)[N:12]([C:10]([O:9][CH2:6][CH:7]=[CH2:8])=[O:11])[CH2:13]1)(=[O:4])[CH3:2]

参加物

6

反応物 2

HCID 23670855Potassium ethanethioateHCID 86756315(3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine

生成物 1

HCID 86756316(3S,5S)-3-Acetylthio-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine収率 41.2%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

Potassium thioacetate (149 mg) is added to a solution of 355 mg of crude (3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine (stereoisomer B) in a mixture of 3 ml of dry DMF and 1.5 ml of dry toluene, and the mixture is stirred in an argon atmosphere at a bath temperature of 80° C. for 12 hr. The mixture is diluted with 100 ml of ethyl acetate and washed twice with 40 ml of a 5% aqueous sodium hydrogencarbonate solution. The organic layer is dried over magnesium sulfate and filtered, and the solvent is removed by evaporation under reduced pressure. The residue is dried under reduced pressure by means of a vacuum pump for 2 hr. The resultant brown oil is successively purified by column chromatography on silica gel (ethyl acetate) and on Sephadex LH-20 (chloroform:methanol=1:1) to give 139.1 mg of the title compound as a slightly red amorphous material.

後処理

  1. washwashed twice with 40 ml of a 5% aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent is removed by evaporation under reduced pressure
  5. customThe residue is dried under reduced pressure by means of a vacuum pump for 2 hr
  6. customThe resultant brown oil is successively purified by column chromatography on silica gel (ethyl acetate) and on Sephadex

出典と根拠

ORDレコード
ord-66db2cf9a49c4d64ab87bd205db7e5ee
出典データセット
uspto-grants-2001_01
特許番号
US06180622B2

反応ノート

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