Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)- → tert-Butyl [1-({3-(3,4-dimethylphenyl)-5-[(phenylcarbonyl)amino]piperidin-1-yl}carbonyl)cyclobutyl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)-	HCID 1512646	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	N-[5-(3,4-dimethylphenyl)piperidin-3-yl]benzamide	HCID 66701309	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dimethylformamide	HCID 6228	—
Product	tert-Butyl [1-({3-(3,4-dimethylphenyl)-5-[(phenylcarbonyl)amino]piperidin-1-yl}carbonyl)cyclobutyl]carbamate	HCID 68075430	—

Reaction Steps

62 mg (0.3 mmol) of 1-[(tert-butoxycarbonyl)amino]cyclobutanecarboxylic acid together with 110 mg (0.3 mmol) of HATU and 47 mg (0.4 mmol) of 4-dimethylaminopyridine were initially charged in 2 ml of DMF, and 60 mg (0.2 mmol) of N-[-5-(3,4-dimethylphenyl)piperidin-3-yl]benzamide were added. The reaction mixture was stirred overnight and then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 54 mg (55% of theory)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987248B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-b546c95fcf194d1ebd45198b8ae0933b
Source note	uspto-grants-2015_03