3-Azido-4-carboethoxy-1-(p-methoxyphenyl)-azetidine-2-one → HCID 19748755, compound

HRID 484038Notes

Reaction equation

HRID 484038 reaction equation
[N:1]([CH:4]1[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:5]1=[O:21])=[N+]=[N-]>C(O)C.[Pd]>[C:8]([CH:7]1[N:6]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:5](=[O:21])[CH:4]1[NH2:1])([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 1

HCID 139222703-Azido-4-carboethoxy-1-(p-methoxyphenyl)-azetidine-2-one

Product 1

HCID 19748755HCID 19748755, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.16 g of 3-azido-4-carboethoxy-1-(p-methoxyphenyl)-azetidine-2-one in ethanol was hydrogenated with palladium to yield 4-carboethoxy-1-(p-methoxyphenyl)-3-aminoazetidin-2-one. This amine was acylated with 1.1 ml of trifluoro acetic anhydride in 10 ml CH2Cl2 containing 1.5 ml pyridine, followed by methylation using 1 ml dimethyl sulfate in 30 ml acetone containing 3 g potassium carbonate. After isolation, the crude product was crystallized to give 2.2 g of 4-carboethoxy-1-(p-methoxyphenyl)-3-(N-methyltrifluoroacetamido)-azetidine-2-one, m.p. 102°-104°.

Sources & evidence

ORD record
ord-339fafad6360487baf7f6922239edfc0
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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