(3S, 4R)-4-(2,2-dimethoxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one → (3S, 4R)-3-(1-methoxy-1-methylethyl)-4-(2-oxoethyl)azetidin-2-one

HRID 235748Notes

Reaction equation

HRID 235748 reaction equation
C[O:2][CH:3](OC)[CH2:4][C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C:10]([O:13][CH3:14])([CH3:12])[CH3:11]>C(O)(=O)C>[CH3:14][O:13][C:10]([C@@H:6]1[C@@H:5]([CH2:4][CH:3]=[O:2])[NH:8][C:7]1=[O:9])([CH3:12])[CH3:11]

Participants

3

Reactant 1

HCID 56633268(3S, 4R)-4-(2,2-dimethoxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one

Product 1

HCID 56638716(3S, 4R)-3-(1-methoxy-1-methylethyl)-4-(2-oxoethyl)azetidin-2-oneYield 92.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (3S, 4R)-4-(2,2-dimethoxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one (1.03 g) in 80% aqueous acetic acid (50 ml) was stirred at 50° C. for 4 hours, and the solution was evaporated in vacuo. The residue was dissolved in toluene (8 ml) and evaporated in vacuo to give (3S, 4R)-3-(1-methoxy-1-methylethyl)-4-(2-oxoethyl)azetidin-2-one (760 mg) as an oil.

Workup

  1. customthe solution was evaporated in vacuo
  2. dissolutionThe residue was dissolved in toluene (8 ml)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-ad42350d90f243768a2e731c8ab37ed0
Source dataset
uspto-grants-1987_02
Patent number
US04640915

Reaction notes

Loading…