Diketene → t-butyl 2-[N-(3-oxobutanoyl)amino]acetate

HRID 342873Notes

Reaction equation

HRID 342873 reaction equation
[NH2:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:10]=[C:11]1[O:15][C:13](=[O:14])[CH2:12]1>C1C=CC=CC=1>[O:15]=[C:11]([CH3:10])[CH2:12][C:13]([NH:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[O:14]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 151417Glycine tert-butyl ester

Product 1

HCID 54366555t-butyl 2-[N-(3-oxobutanoyl)amino]acetateYield 91.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3.93 g (50 mmol) of t-butyl 2-aminoacetate was dissolved in 65 ml of benzene. To the above mixture, 4.41 g (52.5 mmol) of diketene was added dropwise and the reaction mixture was stirred for one hour. The reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and then with water, and dried over anhydrous sodium sulfate. The solvent was distilled away from the reaction mixture under reduced pressure, whereby 9.821 g (91.2%) of the captioned compound was obtained.

Workup

  1. washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate
  2. dry with materialwith water, and dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled away from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-27cd1a250fae4805ac51e15a60f10db7
Source dataset
uspto-grants-1999_01
Patent number
US05859244

Reaction notes

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