Triethylamine → N-(t-butyldimethylsilyl)-4-(2-acetoxyethyl)azetidin-2-one

HRID 345247Notes

Reaction equation

HRID 345247 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]1[NH:10][C:9](=[O:11])[CH2:8]1)(=[O:3])[CH3:2].[C:12]([Si:16]([CH3:19])([CH3:18])Cl)([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>CN(C)C=O>[Si:16]([N:10]1[CH:7]([CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH2:8][C:9]1=[O:11])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 127692252-(4-Oxoazetidin-2-yl)ethyl acetate

Product 1

HCID 13051149N-(t-butyldimethylsilyl)-4-(2-acetoxyethyl)azetidin-2-oneYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2'-acetoxyethyl)-2-azetidinone (50.2 g., 0.32 mole) and t-butyldimethylchlorosilane (50.6 g, 0.335 mole) in 250 ml anhydrous N,N-dimethylformamide is treated at 0° with triethylamine (35.6 g, 0.353 mole). A white precipitate appears immediately. The mixture is stirred for a period of five minutes. It is then partitioned between 1600 ml benzene and 600 ml water. The organic phase is washed an additional four times with water and finally with brine. The benzene solution is then dried over magnesium sulfate and filtered. Evaporation of the filtrate under reduced pressure gives 84.0 g of 1-(t-butyldimethylsilyl)-4-(2'-acetoxyethyl)-2-azetidinone. Recrystallization from pentane gives 68.9 g of product with m.p. 35°.

Workup

  1. customIt is then partitioned between 1600 ml benzene and 600 ml water
  2. washThe organic phase is washed an additional four times with water
  3. dry with materialThe benzene solution is then dried over magnesium sulfate
  4. filtrationfiltered
  5. customEvaporation of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-b8967452ee0a4de9a632b7a07e957ac7
Source dataset
uspto-grants-1991_10
Patent number
US05055573

Reaction notes

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