4-Phenylbutyric Acid → Rac-n-({[(4-chloro-phenyl)-phenyl-methyl]-carbamoyl}-methyl)-4-phenyl-butyramide

Participants

Role	Name	HCID	Charge
Reactant	4-Phenylbutyric Acid	HCID 4775	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	2-Amino-N-[(4-chloro-phenyl)-phenyl-methyl]-acetamide hydrochloride	HCID 67246438	—
Solvent	Acetonitrile	HCID 6342	—
Product	Rac-n-({[(4-chloro-phenyl)-phenyl-methyl]-carbamoyl}-methyl)-4-phenyl-butyramide	HCID 59689148	71%

Reaction Steps

A suspension of 0.32 mmol rac-2-amino-N-[(4-chloro-phenyl)-phenyl-methyl]-acetamide hydrochloride (Example 3.1) in 5 ml acetonitrile was treated successively with 0.32 mmol 4-phenylbutyric acid, 1.61 mmol DIPEA and 0.35 mmol TBTU. The reaction mixture was stirred for 1 hour at room temperature and concentrated. Chromatography (SiO2; dichloromethane/methanol) gave the title compound as a colorless solid. Yield=71%. MS (m/e): 419.3 (MH−, 100%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07964645B2
Source dataset	uspto-grants-2011_06
ORD ID	ord-aae752b60ace44de9d3ee19d8caf7d9e
Source note	uspto-grants-2011_06