Sodium Chloride → N-Acryloyl-L-glutamic acid

HRID 2380688Notes

Reaction equation

HRID 2380688 reaction equation
[OH-].[Na+].[NH2:3][C@H:4]([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:13](Cl)(=[O:16])[CH:14]=[CH2:15].Cl.O.[Cl-].[Na+]>C(OCC)(=O)C.O>[C:13]([NH:3][C@H:4]([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][C:7]([OH:9])=[O:8])(=[O:16])[CH:14]=[CH2:15]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 33032L-Glutamic AcidHCID 21885828Hydrate;hydrochloride

Product 1

HCID 22842573N-Acryloyl-L-glutamic acidYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A reaction flask was charged with 120 ml distilled water, 48.0 g (1.2 mol) of sodium hydroxide and 58.8 g (0.4 mol) of glutamic acid. After cooling to 0° C., acryloyl chloride, 36 g (0.4 mol) was added over 1 hour to the stirred solution. After stirring for an additional 1 hour, the solution was acidified to pH of 2 with the addition of a concentrated HCl-H2O (1:1) solution. After saturation of the solution with sodium chloride, ethyl acetate was used to extract the product. After drying the combined extracts over anhydrous magnesium sulfate, the ethyl acetate was evaporated to recover the crude product in greater than 60% yield. After recrystallization from ethyl acetate the white, crystalline N-acryloylglutamic acid had a melting point of 125°-127° C.

Workup

  1. additionA reaction flask was charged with 120 ml
  2. extractionto extract the product
  3. dry with materialAfter drying the combined extracts over anhydrous magnesium sulfate
  4. customthe ethyl acetate was evaporated
  5. customto recover the crude product in greater than 60% yield
  6. customAfter recrystallization from ethyl acetate the white, crystalline N-acryloylglutamic acid

Sources & evidence

ORD record
ord-3e3e97c34f054215bd59682e913484ac
Source dataset
uspto-grants-1994_11
Patent number
US05369142

Reaction notes

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