Methanol → N-Lauroyl-L-glutamic acid

HRID 1948761Notes

Reaction equation

HRID 1948761 reaction equation
C[OH:2].[C:3]([NH:16][C@@H:17]1[C:23](=[O:24])[O:22][C:20](=[O:21])[CH2:19][CH2:18]1)(=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C(Cl)Cl.N1C=CC=CC=1>[C:3]([NH:16][C@H:17]([C:23]([OH:22])=[O:24])[CH2:18][CH2:19][C:20]([OH:2])=[O:21])(=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 887MethanolHCID 11335921lauroylglutamic acid anhydride

Product 1

HCID 93133N-Lauroyl-L-glutamic acidYield 84.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

10.00 g (0.00892 mol) of mono-terminal carbinol-modified silicone was dissolved in 10.00 g of methylene chloride and 1.00 g of pyridine. 4.67 g (0.0150 mol) of lauroylglutamic acid anhydride was added to the reaction mixture, and then the mixture was stirred overnight. The reaction liquid was concentrated and separated after adding hexane and a 90% methanol aqueous solution. The hexane layer was concentrated to obtain 10.64 g (0.00753 mol) of lauroylglutamic acid-modified silicone.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated
  3. customseparated
  4. additionafter adding hexane
  5. concentrationThe hexane layer was concentrated

Sources & evidence

ORD record
ord-ceb6765a293a4f829ee769b708f6d8a9
Source dataset
uspto-grants-2013_03
Patent number
US08399524B2

Reaction notes

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