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Hydrochloric Acid → (3S,4R)-3-[(1R)-1-hydroxyethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxo ethyl)-1-[4-nitrobenzyloxycarbonyl(triphenyl phosphoranylidene)methyl]azetidin-2-one

HRID 230042
ノート
印刷プレビュー

反応式

HRID 230042 の反応式
Cl.[Si]([O:9][C@@H:10]([C@@H:12]1[C@@H:15]([C@@H:16]([CH3:35])[C:17]([C:19]2[S:23][C:22]3=[C:24]([C:27]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[O:28])[N:25]=[CH:26][N:21]3[CH:20]=2)=[O:18])[N:14]([C:36]([C:56]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][C:63]([N+:66]([O-:68])=[O:67])=[CH:62][CH:61]=2)=[O:57])=[P:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:13]1=[O:69])[CH3:11])(C(C)(C)C)(C)C.C(=O)(O)[O-].[Na+]>CO>[OH:9][C@@H:10]([C@@H:12]1[C@@H:15]([C@@H:16]([CH3:35])[C:17]([C:19]2[S:23][C:22]3=[C:24]([C:27]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[O:28])[N:25]=[CH:26][N:21]3[CH:20]=2)=[O:18])[N:14]([C:36]([C:56]([O:58][CH2:59][C:60]2[CH:61]=[CH:62][C:63]([N+:66]([O-:68])=[O:67])=[CH:64][CH:65]=2)=[O:57])=[P:37]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:13]1=[O:69])[CH3:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86619389(3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl}-1-[4-nitrobenzyloxycarbonyl(triphenylphosphoranylidene)-methyl]azetidin-2-one

生成物 1

HCID 86619388
(3S,4R)-3-[(1R)-1-hydroxyethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxo ethyl)-1-[4-nitrobenzyloxycarbonyl(triphenyl phosphoranylidene)methyl]azetidin-2-one
収率 73.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A 5 N aqueous hydrochloric acid solution (1 ml) was added to a solution of 72.4 mg of (3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl}-1-[4-nitrobenzyloxycarbonyl(triphenylphosphoranylidene)-methyl]azetidin-2-one in 2 ml of methanol, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution and was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and the residue was purified by thin layer chromatography (developed with 10% methanol/methylene chloride) to give 46.9 mg of (3S,4R)-3-[(1R)-1-hydroxyethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl}-1-[4-nitrobenzyloxycarbonyl(triphenyl phosphoranylidene)methyl]azetidin-2-one.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by evaporation
  5. customthe residue was purified by thin layer chromatography (developed with 10% methanol/methylene chloride)

出典と根拠

ORDレコード
ord-e36a61e4244247bf9e16eb28e2df63ac
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07563901B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート