Ethanolamine → Oleoylethanolamide

HRID 1506730Notes

Reaction equation

HRID 1506730 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5](O)(=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CCCCCC>[CH3:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]/[CH:14]=[CH:13]\[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([NH:4][CH2:3][CH2:1][OH:2])=[O:23]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 445639Oleic Acid

Product 1

HCID 5283454Oleoylethanolamide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

This experiment was carried out according to the procedure of using free fatty acid as acyl donor (Plastina et al., Lett. Org. Chem. 6:444-47 (2009), which is hereby incorporated by reference in its entirety). Ethanolamine (1 mmol) in hexane (1 mL) was mixed with oleic acid (1 mmol) in a 10-mL round bottom flask in the presence of the lipase (50%, relative to total reactants). The reaction was conducted with agitation at ambient temperature for 4, 8, and 24 hours or at 65° C. for 4, 8, and 20 hours before hexane was removed under reduced pressure.

Workup

  1. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-cede5e0578dc4e04bf70b5cae46b2afe
Source dataset
uspto-grants-2015_12
Patent number
US09221747B2

Reaction notes

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