Diketene → HCID 53467999, compound

HRID 1055250Notes

Reaction equation

HRID 1055250 reaction equation
Cl.[NH2:2][C@@H:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:10]=[C:11]1[O:15][C:13](=[O:14])[CH2:12]1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[O:15]=[C:11]([CH3:10])[CH2:12][C:13]([NH:2][C@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:9])=[O:14]

Participants

5

Reactant 3

HCID 12661DiketeneHCID 516892Sodium BicarbonateHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 53467999HCID 53467999, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.00 g (0.13 mol) of ethyl (2S)-2-aminopropanoate hydrochloride were added to a solution of 10.95 g (0.13 mol) of diketene in 500 ml toluene at 0° C. Then, 21.90 g (0.26 mol) NaHCO3 was added and the reaction mixture was stirred overnight at room temperature. Since no more starting material was detected by thin-layer chromatography, the reaction mixture was filtered, evaporated and the residue purified by column chromatography. This gave 19.36 g (0.096 mol, 74% yield) of a colorless oil.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated
  3. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-248ffad6c5e744ed861cec099db7bc06
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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