Ammonium Acetate → tert-Butyl [(2S,3S)-2-methyl-4-oxoazetidin-3-yl]carbamate

HRID 279811Notes

Reaction equation

HRID 279811 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH3:13])[N:11](O)[C:10]1=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+]>CO.[Cl-].[Na+].[Cl-].[Cl-].[Cl-].[Ti+3]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH3:13])[NH:11][C:10]1=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 517165Ammonium AcetateHCID 12946603tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamate

Product 1

HCID 13155285tert-Butyl [(2S,3S)-2-methyl-4-oxoazetidin-3-yl]carbamateYield 71.6%

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolventHCID 5234Sodium ChlorideSolvent

Procedure

A solution of 4.98 g of (3S-trans)-3-t-butoxycarbonylamino-1-hydroxy-4-methylazetidinone in 200 ml of methanol was treated with 132 ml of 4.5 M ammonium acetate and then 66 ml of 1.5 titanium trichloride and stirred for 4.5 hours. The aqueous solution was diluted with an equal volume of 8% sodium chloride and extracted with ethyl acetate to give 3.48 g of crude product. Recrystallization from ether-hexane yielded 3.3 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. customto give 3.48 g of crude product
  3. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-f5b08df4a7fd4950a04448f76ec1313a
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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