Methanol → N-Lauroyl-L-glutamic acid

HRID 1287561Notes

Reaction equation

HRID 1287561 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].CO.[OH-].[Na+].S(=O)(=O)(O)O.[C:20](O)(=[O:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]CCCC>O>[C:20]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])(=[O:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 33032L-Glutamic AcidHCID 86734071HCID 86734071, compound

Product 1

HCID 93133N-Lauroyl-L-glutamic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-Glutamic acid 2.9 g was dissolved in 30 ml water and 30 ml methanol and 1.6 g of sodium hydroxide. To this solution was added 8.8 g of the crystal of palmitic acid sulfuric acid mixed anhydride and 10 N sodium hydroxide to keep pH 12 to 13, with stirring at 21° - 22°C. The reaction mixture was stirred for an additional 1 hour, and then treated by the same manner as in Example 1. N-Lauroyl-L-glutamic acid was obtained. Yield 6.4 g (96.9%). M.P. 101° - 104.5°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-eb3996f560784f09ab4486965a0d2c64
Source dataset
uspto-grants-1976_10
Patent number
US03985722

Reaction notes

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