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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 1708522
ノート
印刷プレビュー

反応式

HRID 1708522 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].O1CCCC1>[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 90%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of sodium hydrogen carbonate (0.84 g) in water (10 ml), dimedone (0.84 g) and tetrahydrofuran (80 ml) is treated with ultrasonics, and thereto is added palladium diacetate (0.11 g) and triethyl phosphite (0.58 g) under nitrogen atmosphere, and the mixture is stirred for three minutes. To the mixture is added (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid allyl ester (3.83 g), and the mixture is stirred at 35°-37° C. for 45 minutes. The mixture is stirred at 5° C. for 30 minutes, and the precipitated crystals are collected by filtration, washed with tetrahydrofuran, and dried under reduced pressure to give (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-carbapen- 2-em-3-carboxylic acid sodium salt (3.28 g).

後処理

  1. additionis treated with ultrasonics
  2. stirringthe mixture is stirred at 35°-37° C. for 45 minutes
  3. stirringThe mixture is stirred at 5° C. for 30 minutes
  4. filtrationthe precipitated crystals are collected by filtration
  5. washwashed with tetrahydrofuran
  6. customdried under reduced pressure

出典と根拠

ORDレコード
ord-6528f2662cb549b4b9d1296290a6d8f1
出典データセット
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05359059

反応ノート

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