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 1081948노트

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HRID 1081948 반응식
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]

참가 물질

9

반응물 5

HCID 31215Triethyl phosphiteHCID 312751,4-DioxaneHCID 31358DimedoneHCID 516892Sodium BicarbonateHCID 10720094HCID 10720094, 화합물

생성물 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 salt수율 91.9%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 3283Diethyl Ether용매

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온도
30 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dc42c43e0c094e16916fc0cb4a7f0c50
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05587474

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