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

HRID 1421826Notes

Reaction equation

HRID 1421826 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-96253e8b7417433cb617601b6e80ef20
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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