N-Lauroyl-L-glutamic acid → lauroylglutamic acid anhydride

HRID 595606Notes

Reaction equation

HRID 595606 reaction equation
[C:1]([NH:14][C@H:15]([C:21]([OH:23])=[O:22])[CH2:16][CH2:17][C:18]([OH:20])=O)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C(OC(=O)C)(=O)C>[C:1]([NH:14][C@@H:15]1[C:21](=[O:22])[O:23][C:18](=[O:20])[CH2:17][CH2:16]1)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 1

HCID 93133N-Lauroyl-L-glutamic acid

Product 1

HCID 11335921lauroylglutamic acid anhydrideYield 76.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

100 g of Nα-lauroyl-L-glutamic acid was heated with stirring for 5 hours at 60° C. in 200 g of acetic anhydride, and then cooled to room temperature with stirring to allow a crystal to precipitate. This crystal was washed with 1000 mL of hexane and dried to obtain 72.4 g of Nα-lauroyl-L-glutamic anhydride.

Workup

  1. customto precipitate
  2. washThis crystal was washed with 1000 mL of hexane
  3. customdried

Sources & evidence

ORD record
ord-4de219f6db77487ab460883e7e109d91
Source dataset
uspto-grants-2016_01
Patent number
US09243075B2

Reaction notes

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