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

HRID 1421826노트

반응식

HRID 1421826 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-96253e8b7417433cb617601b6e80ef20
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077952

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