4-Methylmorpholine → N-(3-Phenylpropionyl)-L-prolyl-L-proline benzyl ester

https://huagongshe.com/reaction/1720490

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	Dicyclohexylcarbodiimide	HCID 10868	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Proline benzyl ester hydrochloride	HCID 2733413	—
Reactant	L-Proline, 1-(1-oxo-3-phenylpropyl)-	HCID 10354601	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(3-Phenylpropionyl)-L-prolyl-L-proline benzyl ester	HCID 54563213	79.1%

Reaction Conditions

Temperature	-25 °C

Reaction Steps

To L-proline benzyl ester hydrochloride (0.98 g) in dichloromethane (20 ml) were added N-methylmorpholine (0.49 ml), N-(3-phenylpropionyl)-L-proline (1.00 g) and HOBt (0.60 g) under ice-cooling. After cooling to -25° C. , DCC (0.92 g) was added, and the mixture was stirred at a temperature between -25° C. and 0° C. for 2 hours, and then at room temperature for 14 hours. The reaction mixture was treated and purified as in Example 7-A) to give 1.39 g of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05506256
Source dataset	uspto-grants-1996_04
ORD ID	ord-ca8de61c60974b23bf640984089acfec
Source note	uspto-grants-1996_04