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

HRID 867644Notes

Reaction equation

HRID 867644 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]carbamate

Reagents, catalysts & solvents 3

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

Procedure

A solution of 4.98 of (3S-trans)-3-t-butoxycarbonylamino-1-hydroxy-4-methylazetidinone in 200 ml of methanol is treated with 132 ml of 4.5M ammonium acetate and then 66 ml of 1.5M titanium trichloride and stirred for 4.5 hours. The aqueous solution is 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 yields 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-73b3ea52cda147bb886fa1ce3731902e
Source dataset
uspto-grants-1988_10
Patent number
US04775670

Reaction notes

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