Diisopropylethylamine → HCID 131723228, compound

https://huagongshe.com/reaction/1937814

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733286	—
Reactant	Methyl (2S)-amino(cyclohexyl)acetate--hydrogen chloride (1/1)	HCID 17747951	—
Reactant	HCID 22667660	HCID 22667660	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 131723228	HCID 131723228	—

Reaction Conditions

Temperature	-10 °C

Reaction Steps

2-(R,S)-(4-Cyano-benzyl)-N,N-dimethyl-malonamic acid (10 g, 40.6 mmol) and L-cyclohexylglycine methylester hydrochloride (8.3 g, 40 mmol) were dissolved in dimethylformamide (500 ml). After cooling to −10° C. TOTU (13.1 g, 40 mmol) and diisopropylethylamine (10.34 g, 80 mmol) were added. The mixture was stirred for 1 hour and then allowed to warm to room temperature. After evaporation ethyl acetate was added to the residue and the organic layer was extracted with aqueous sodium hydogen carbonate solution, potassium hydrogen sulfate solution and water. The organic layer was evaporated. Yield: 14.53 g (90%); MS m/z: 400.3 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06395737B1
Source dataset	uspto-grants-2002_05
ORD ID	ord-6da3d8a95b41443bbc9f7fa99ce9cd3b
Source note	uspto-grants-2002_05