HCID 70489672, compound → HCID 54191506, compound

HRID 851385Notes

Reaction equation

HRID 851385 reaction equation
C([N:7]1[C:10](=[O:11])[C@H:9]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[C@H:8]1[CH2:23][C:24](=[O:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27])(C(OC)=O)=O>CO>[O:30]=[C:24]([CH2:23][C@@H:8]1[C@@H:9]([N:12]2[C:13](=[O:22])[C:14]3=[CH:21][CH:20]=[CH:19][CH:18]=[C:15]3[C:16]2=[O:17])[C:10](=[O:11])[NH:7]1)[CH2:25][C:26]([O:28][CH3:29])=[O:27]

Participants

3

Reactant 1

HCID 70489672HCID 70489672, compound

Product 1

HCID 54191506HCID 54191506, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-[(2R,3R)-1-methoxalyl-4-oxo-3-phthalimidoazetidin-2-yl]-3-oxobutanoate (68 mg) in methanol (4 ml) was stirred at room temperature for 16 hours and heated at 55°-60° C. for two hours. The resultant solution was evaporated, and the residue was chromatographed on a silica gel plate (developing solvent: 20% acetone in dichloromethane) to afford methyl 3-oxo-4-[(2R,3R)-4-oxo-3-phthalimidoazetidin-2-yl]butanoate (35 mg) as an amorphous solid. Crystallization from a mixture of ethyl acetate and ether gave crystals (26 mg), mp 120°-124° C.

Workup

  1. temperatureheated at 55°-60° C. for two hours
  2. customThe resultant solution was evaporated
  3. customthe residue was chromatographed on a silica gel plate (developing solvent: 20% acetone in dichloromethane)

Sources & evidence

ORD record
ord-e26728c9d9aa46fca5fdac5e29c1779b
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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