Triethylamine → 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-N-methoxy-2,N-dimethyl-benzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Hydroxyamine hydrochloride	HCID 443297	—
Reactant	4-{1-[4-(3,3-Dimethyl-2-hydroxybutoxy)-3-methylphenyl]-1-ethylpropyl}-2-methylbenzoic acid	HCID 10364368	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-N-methoxy-2,N-dimethyl-benzamide	HCID 57763441	128.8%

Reaction Steps

To mixture of enantiomer 2 of 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid (0.70 g, 1.70 mmol) and DMF (5 mL) is added hydroxylamine hydrochloride (0.18 g, 1.87 mmol), EDCI (0.33 g, 1.87 mmol), HOBt (0.23 g, 1.87 mmol), and NEt3 (0.95 mL, 6.79 mmol). The mixture is stirred at ambient temperature overnight, diluted with EtOAc (40 mL), washed with 1M HCl (40 mL), water (40 mL), brine (40 mL), dried over MgSO4, filtered and concentrated to furnish the title compound (0.76 g, 2.19 mmol, 81%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07566803B2
Source dataset	uspto-grants-2009_07
ORD ID	ord-2159f28153cc496dad4240ed04190b0e
Source note	uspto-grants-2009_07