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Triethyl phosphite → (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylic acid sodium salt

HRID 1081947
ノート
印刷プレビュー

反応式

HRID 1081947 の反応式
C(=O)([O-])O.[Na+:5].CC1(C)CC(=O)CC(=O)C1.P(OCC)(OCC)OCC.C([O:29][C:30]([C:32]1[N:36]2[C:37](=[O:42])[C@H:38]([C@H:39]([OH:41])[CH3:40])[C@H:35]2[C@@H:34]([CH3:43])[C:33]=1[S:44][C@H:45]1[CH2:49][NH:48][C:47](=[S:50])[CH2:46]1)=[O:31])C=C>O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(O)C>[Na+:5].[NH:48]1[CH2:49][C@H:45]([S:44][C:33]2[C@H:34]([CH3:43])[C@@H:35]3[C@@H:38]([C@H:39]([OH:41])[CH3:40])[C:37](=[O:42])[N:36]3[C:32]=2[C:30]([O-:31])=[O:29])[CH2:46][C:47]1=[S:50]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 31215Triethyl phosphiteHCID 31358DimedoneHCID 516892Sodium BicarbonateHCID 10571982HCID 10571982、化合物

生成物 1

HCID 23689827(1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylic acid sodium salt収率 43.1%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 702Ethanol溶媒
HCID 962Water溶媒

実験手順

To a solution of sodium hydrogen carbonate (84 mg) in water (1 ml) is added dimedone (84 mg), and the mixture is dissolved by treating with ultrasonics. Thereto is added ethanol (8 ml), and further treated with ultrasonics for five minutes. To the mixture are added palladium diacetate (11 mg), triethyl phosphite (0.06 ml) and (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid allyl ester (383 mg) under nitrogen atmosphere, and the mixture is stirred at 35°-38° C. for one hour, and stirred at 20° C. for 10 minutes, and then stirred at 5° C. for 20 minutes. The precipitated crystals are collected by filtration to give (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt (157 mg). The mother liquor is concentrated under reduced pressure to remove the ethanol, and thereto is added water (20 ml). The mixture is washed five times with chloroform (20 ml), and the aqueous layer is subjected to lyophilization to give the above sodium salt (168 mg).

後処理

  1. dissolutionthe mixture is dissolved
  2. additionby treating with ultrasonics
  3. additionfurther treated with ultrasonics for five minutes
  4. stirringstirred at 20° C. for 10 minutes
  5. stirringstirred at 5° C. for 20 minutes
  6. filtrationThe precipitated crystals are collected by filtration

出典と根拠

ORDレコード
ord-a825ad4ffdf040899b94f240c0162af5
出典データセット
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05587474

反応ノート

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