DL-Glutamic acid → N-Lauroyl-DL-glutamic acid

HRID 1287560

Reaction equation

HRID 1287560 reaction equation
[NH2:1][CH:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[OH-].[Na+].N[C@H](C([O-])=O)CCC([O-])=O.[Na+].[Na+].[C:25](O)(=[O:37])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].S(=O)(=O)(O)O>O.CC(C)=O>[C:25]([NH:1][CH:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])(=[O:37])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 611DL-Glutamic acidHCID 14798Sodium Hydroxide2×HCID 167560Disodium glutamateHCID 19758976Lauric acid sulfuric acid

Product 1

HCID 351563N-Lauroyl-DL-glutamic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

DL-Glutamic acid 14.7 g was suspended in 75 ml water and 45 ml acetone and then added 8 g of sodium hydroxide. To the solution of the sodium glutamate was added lauric acid-sulfuric acid mixed anhydride with 10 N sodium hydroxide at pH 12 - 13 on the ice bath with stirring. The reaction mixture was stirred for an additional 1 hour, then treated by the same manner as in Example 1. N-Lauroyl-DL-glutamic acid was obtained 19.7 g (59.7 %) M.P. 116° - 119°C.

Workup

  1. stirringThe reaction mixture was stirred for an additional 1 hour
  2. additiontreated by the same manner as in Example 1

Sources & evidence

ORD record
ord-facafe52fdfa4251be80681e2badce34
Source dataset
uspto-grants-1976_10
Patent number
US03985722

Linked notes

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