Reaction #53625

ord-f5ac59a7fb8540c8a6d0e1f04c8cecc0

Reaction equation

glycine ethyl ester

glycinamide

EDCI

$CCCCCCCC/C=C\CCCCCCCC(=O)N(C)CC(=O)O$

N-Oleoyl sarcosine

$CCCCCCCC/C=C\CCCCCCCC(=O)O$

oleic acid

→

$CCCCCCCC/C=C\CCCCCCCC(=O)NCC(=O)O$

N-Oleoyl glycine

Reactants

$CCCCCCCC/C=C\CCCCCCCC(=O)N(C)CC(=O)O$

N-Oleoyl sarcosine

—

ethyl ester

$CCCCCCCC/C=C\CCCCCCCC(=O)O$

oleic acid

Reagents

None

Solvents

EtOH

Conditions

Detailed conditions

See reaction.notes.procedure_details.

Procedure

N-Oleoyl glycine (FIG. 7) was prepared by coupling glycine ethyl ester to oleic acid with EDCI (Cravatt et al. (1996) J. Am. Chem. Soc. 118, 580-590; Patterson et al. (1996) J. Am. Chem. Soc. 118, 5938-5945) followed by sequential transformation to the carboxylic acid (LiOH) and glycinamide (EDCI, NH4OH;). N-Oleoyl sarcosine was purchased (Pfaltz and Bauer) and converted to its ethyl ester by coupling with EtOH (DCC).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858649B1uspto-grants-2005_02