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

HRID 371213
Notes
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Reaction equation

HRID 371213 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887MethanolSolvent
HCID 5234
Sodium Chloride
Solvent

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-22fefcd4befb4e579abeb47ab64c7ff3
Source dataset
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04529698

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes