Diazomethane → HCID 12832739, compound

HRID 851379Notes

Reaction equation

HRID 851379 reaction equation
[O:1]=[C:2]1[CH2:5][C@@H:4]([CH2:6][CH:7]2[O:11][CH2:10]O[O:8]2)[N:3]1C(=O)C(OC)=O.[N+](=C)=[N-]>CO.C(OCC)C>[O:1]=[C:2]1[NH:3][C@@H:4]([CH2:6][C:7]([O:11][CH3:10])=[O:8])[CH2:5]1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 53882539HCID 53882539, compound

Product 1

HCID 12832739HCID 12832739, compoundYield 17.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl [(4R)-2-oxo-4-(1,2,4-trioxolan-3-ylmethyl)azetidin-1-yl]glyoxylate (60 mg) in methanol (5 ml) was heated at 65°-70° for two hours. The yellowish solution was cooled to 0° C. and treated with a solution of diazomethane (excess) in diethyl ether. After removal of the solvent, the residue was chromatographed on silica gel (1.5 g) eluting with 20% acetone in dicloromethane to give methyl 2-[(2R)-4-oxoazetidin-2-yl]acetate (6 mg).

Workup

  1. customAfter removal of the solvent
  2. customthe residue was chromatographed on silica gel (1.5 g)
  3. washeluting with 20% acetone in dicloromethane

Sources & evidence

ORD record
ord-7b6a6342b6da434bbe58b2b32bf1af97
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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