HCID 10086774, compound → cis-3-acetoxy-4-phenylazetidin-2-one

HRID 865626Notes

Reaction equation

HRID 865626 reaction equation
COC1C=CC([N:9]2[C@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:11]([O:19][C:20](=[O:22])[CH3:21])[C:10]2=[O:23])=CC=1>C(#N)C.O>[C:20]([O:19][C@H:11]1[C@@H:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:9][C:10]1=[O:23])(=[O:22])[CH3:21]

Participants

4

Reactant 1

HCID 10086774HCID 10086774, compound

Product 1

HCID 11009062cis-3-acetoxy-4-phenylazetidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The above procedure may, in turn, be followed by modification of the lactam formed, should a different lactam starting material be desired. For example, a cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one racemate prepared as above, in acetonitrile at a temperature such as -10° C. to -5° C., may be treated with a solution of ceric ammonium nitrate in water to yield a cis-3-acetoxy-4-phenylazetidin-2-one racemate. The latter compound may, for example, further be hydrolyzed, e.g., with aqueous potassium hydroxide, to yield cis-3-hydroxy-4-phenylazetidin-2-one.

Workup

  1. customformed
  2. customsuch as -10° C. to -5° C.

Sources & evidence

ORD record
ord-ded21d337e2a41c299ec0d0226c06e7e
Source dataset
uspto-grants-1996_10
Patent number
US05567614

Reaction notes

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