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

HRID 1081948ノート

反応式

HRID 1081948 の反応式
CC1(C)CC(=O)CC(=O)C1.O1CCOCC1.P(OCC)(OCC)OCC.C([O:30][C:31]([C:33]1[N:37]2[C:38](=[O:50])[C@H:39]([C@H:40]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[CH3:41])[C@H:36]2[C@@H:35]([CH3:51])[C:34]=1[S:52][C@H:53]1[CH2:57][NH:56][C:55](=[S:58])[CH2:54]1)=[O:32])C=C.C(=O)([O-])O.[Na+:63]>O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(OCC)C>[Na+:63].[NH:56]1[CH2:57][C@H:53]([S:52][C:34]2[C@H:35]([CH3:51])[C@@H:36]3[C@@H:39]([C@H:40]([O:42][Si:43]([C:46]([CH3:48])([CH3:47])[CH3:49])([CH3:44])[CH3:45])[CH3:41])[C:38](=[O:50])[N:37]3[C:33]=2[C:31]([O-:32])=[O:30])[CH2:54][C:55]1=[S:58]

参加物

9

反応物 5

HCID 31215Triethyl phosphiteHCID 312751,4-DioxaneHCID 31358DimedoneHCID 516892Sodium BicarbonateHCID 10720094HCID 10720094、化合物

生成物 1

HCID 23709518(1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt収率 91.9%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
30 °C

実験手順

Dimedone (169 mg) is dissolved in a solution of sodium hydrogen carbonate (169 mg) in water (2 ml) by ultrasonic treatment, and thereto are added dioxane (16 ml), palladium diacetate (23 mg) and triethyl phosphite (0.12 ml) under nitrogen atmosphere, and further added thereto (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid allyl ester (1.03 g). The mixture is stirred at 30° C. for 30 minutes, and thereto is added diethyl ether (32 ml), and the mixture is stirred at 25° C. for 15 minutes, and further stirred at 5° C. for 30 minutes. The precipitated crystals are collected by filtration, washed with diethyl ether, and dried under reduced pressure at 25° C. for 17 hours to give (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt (885 mg).

後処理

  1. additionfurther added
  2. stirringthe mixture is stirred at 25° C. for 15 minutes
  3. stirringfurther stirred at 5° C. for 30 minutes
  4. filtrationThe precipitated crystals are collected by filtration
  5. washwashed with diethyl ether
  6. customdried under reduced pressure at 25° C. for 17 hours

出典と根拠

ORDレコード
ord-dc42c43e0c094e16916fc0cb4a7f0c50
出典データセット
uspto-grants-1996_12
特許番号
US05587474

反応ノート

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