Ethylmorpholine → 3-Hydroxypyridine-2-carboxylic acid N-(((1-dodecyloxy)carbonyl)methyl)amide

Participants

Role	Name	HCID	Charge
Reactant	Ethylmorpholine	HCID 7525	—
Reactant	3-Hydroxypicolinic Acid	HCID 13401	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	N-cyclohexyl-N'-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonate	HCID 9954069	—
Reactant	Glycine 1-dodecyl ester tosylate	HCID 15435490	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-Hydroxypyridine-2-carboxylic acid N-(((1-dodecyloxy)carbonyl)methyl)amide	HCID 9842011	—

Reaction Conditions

Temperature	20 °C

Reaction Steps

7 g (50 mmol) of 3-hydroxypyridine-2-carboxylic acid were suspended in 800 ml of anhydrous dichloromethane and treated with 7.5 g (55 mmol) of 1-hydroxy-1H-benzotriazole, 19.2 ml (150 mmol) of N-ethylmorpholine, 21.2 g (50 mmol) of N-cyclohexyl-N'-(2-morpholinoethyl)carbodiimide methyl-p-toluenesulfonate (CMC) and 20.8 g (50 mmol) of glycine 1-dodecyl ester tosylate and the mixture was stirred at 20° C. for 50 h.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06020350
Source dataset	uspto-grants-2000_02
ORD ID	ord-015e862b3cb0448ab6bfcf1d5e1d4c92
Source note	uspto-grants-2000_02