Potassium Carbonate → (3R,4R)-4-[(2RS,5SR)-5-Methoxycarbonyltetrahydrofuran-2-ylcarbonylmethylthio)-3-phenylacetamidoazetidin-2-one

HRID 1421826ノート

反応式

HRID 1421826 の反応式
C(=O)([O-])[O-].[K+].[K+].[SH:7][C@H:8]1[NH:11][C:10](=[O:12])[C@H:9]1[NH:13][C:14](=[O:22])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl[CH2:24][C:25]([CH:27]1[O:31][CH:30]([C:32]([O:34][CH3:35])=[O:33])[CH2:29][CH2:28]1)=[O:26]>CN(C)C=O>[CH3:35][O:34][C:32]([CH:30]1[O:31][CH:27]([C:25]([CH2:24][S:7][C@H:8]2[NH:11][C:10](=[O:12])[C@H:9]2[NH:13][C:14](=[O:22])[CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:26])[CH2:28][CH2:29]1)=[O:33]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 13944080(3R,4R)-4-mercapto-3-phenylacetamidoazetidin-2-oneHCID 71435111Methyl (2RS,5SR)-5-(2-chloroacetyl)tetrahydro-2-furoate

生成物 1

HCID 67907703(3R,4R)-4-[(2RS,5SR)-5-Methoxycarbonyltetrahydrofuran-2-ylcarbonylmethylthio)-3-phenylacetamidoazetidin-2-one収率 55.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Potassium carbonate (2.0 g) was added to a stirred solution of (3R,4R)-4-mercapto-3-phenylacetamidoazetidin-2-one (2.31 g) and methyl (2RS,5SR)-5-(2-chloroacetyl)tetrahydro-2-furoate (2.02 g) in dimethylformamide (30 ml). The mixture was stirred at room temperature for 1.5 h and then partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed three times with water, then brine, dried over magnesium sulphate and evaporated. The title compound (2.208 g) was isolated by column chromatography of the residue (silica gel, ethyl acetate as eluent); νmax (CHCl3) 3410, 3335, 1777, 1736 and 1678 cm -1.

後処理

  1. custompartitioned between ethyl acetate and water
  2. customThe aqueous phase was separated
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed three times with water
  5. dry with materialbrine, dried over magnesium sulphate
  6. customevaporated

出典と根拠

ORDレコード
ord-96253e8b7417433cb617601b6e80ef20
出典データセット
uspto-grants-2000_06
特許番号
US06077952

反応ノート

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