Potassium Carbonate → (3s-trans)-3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-(phenylmethoxy)azetidine

HRID 2165276Notes

Reaction equation

HRID 2165276 reaction equation
C(=O)([O-])[O-].[K+].[K+].N#N.[C:9]([O:13][C:14]([NH:16][C@H:17]([C:25]([NH:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:26])[C@@H:18]([CH3:24])OS(C)(=O)=O)=[O:15])([CH3:12])([CH3:11])[CH3:10]>O.ClCCCl>[C:9]([O:13][C:14]([NH:16][C@H:17]1[C@H:18]([CH3:24])[N:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:25]1=[O:26])=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86744082N2 (t-Butyloxycarbonyl)-O-(methylsulfonyl)-N-(phenylmethoxy)-L-threonineamid

Product 1

HCID 12946599(3s-trans)-3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-(phenylmethoxy)azetidineYield 60.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

Potassium carbonate (200g) was dissolved in 300ml of water, 1.5 liters of 1,2-dichloroethane was added, and the mixture was refluxed. A suspension of 178 g of N2 -(t-Butyloxycarbonyl)-O-(methylsulfonyl)-N-(phenylmethoxy)-L-threonineamide in 1.2-dichloroethane was added and the mixture was refluxed for 2 hours. The layers were cooled and the organic layer was evaporated, redissolved in ethyl acetate, washed twice with water, dried (MgSO4) and evaporated again. The oily residue crystallized on treatment with petroleum ether, yielding 76.7 g of the title compound, melting point 78° C.

Workup

  1. temperaturethe mixture was refluxed
  2. additionwas added
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperatureThe layers were cooled
  5. customthe organic layer was evaporated
  6. dissolutionredissolved in ethyl acetate
  7. washwashed twice with water
  8. dry with materialdried (MgSO4)
  9. customevaporated again
  10. customThe oily residue crystallized on treatment with petroleum ether

Sources & evidence

ORD record
ord-e13a79c4247f4a22956ceceac9e91254
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

Loading…