Dimethyl Sulfoxide → HCID 86756330、化合物

HRID 568290ノート

反応式

HRID 568290 の反応式
CC(C)([O-])C.[K+].[Cl-].[S:8]1[CH:12]=[CH:11][N:10]2[C:13]([CH2:16][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:14][CH:15]=[C:9]12.[CH2:36]([O:39][C:40]([N:42]1[C@H:46]([CH:47]=O)[CH2:45][C@@H:44]([O:49][Si](C(C)(C)C)(C)C)[CH2:43]1)=[O:41])[CH:37]=[CH2:38].C(OCC)(=[O:59])C.C[S:64]([CH3:66])=[O:65]>C1COCC1>[CH2:36]([O:39][C:40]([N:42]1[C@H:46]([CH:47]=[CH:16][C:13]2[N:10]3[C:9]([S:8][CH:12]=[CH:11]3)=[CH:15][N:14]=2)[CH2:45][C@@H:44]([O:49][S:64]([CH3:66])(=[O:59])=[O:65])[CH2:43]1)=[O:41])[CH:37]=[CH2:38]

参加物

7

反応物 5

HCID 679Dimethyl SulfoxideHCID 8857Ethyl AcetateHCID 21262400HCID 21262400、化合物HCID 22870383(2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 86756330HCID 86756330、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Potassium t-butoxide (0.11 g) is added to a solution of 0.44 g of (imidazo[5,1-b]thiazol-5-yl)methyltriphenylphosphonium chloride in 2 ml of THF and 2 ml of dimethyl sulfoxide under ice cooling. The mixture is stirred at that temperature for one hr, and a solution of 0.28 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-formylpyrrolidine in 2 ml of THF, and the mixture is stirred at that temperature for 2 hr. Ethyl acetate is added to the reaction mixture, and the mixture is successively washed with dilute hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation, and the residue is purified by column chromatography on silica gel (methanol:ethyl acetate=5:95) to give 0.33 g of (3R,5S)-1-allyloxycarbonyl-5-[2-(imidazo[5,1-b]thiazol-5-yl)ethenyl]-3-methanesulfonyloxypyrrolidine (a mixture of geometrical isomers).

後処理

  1. washthe mixture is successively washed with dilute hydrochloric acid
  2. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated saline and dried over anhydrous magnesium sulfate
  3. customThe solvent is removed by evaporation
  4. customthe residue is purified by column chromatography on silica gel (methanol:ethyl acetate=5:95)

出典と根拠

ORDレコード
ord-926aefcf4dd04b8a8d2dcd8d37ed5b94
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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