Hydrochloric Acid → HCID 68635424, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Salicylic Acid	HCID 338	—
Reactant	Diisopropylethylamine	HCID 81531	—
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	Benzyl (2-amino-2-methylpropyl)carbamate	HCID 15236683	—
Solvent	Acetonitrile	HCID 6342	—
Product	HCID 68635424	HCID 68635424	26%

Reaction Steps

The HCl salt of benzyl 2-amino-2-methylpropylcarbamate (1.0 g, 3.87 mmol) was taken up in CH3CN (15 mL) along with HATU (1.60 g, 4.2 mmol), salicylic acid (535 mg. 3.87 mmol) and DIEA (2.0 mL, 11.6 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3, brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by chromatography (30% EtOAc/pentane) to afford benzyl 2-(2-hydroxybenzamido)-2-methylpropylcarbamate (340 mg, 26%). Mass calculated for C19H22N2O4: 342.16; found: [M+H]+=343.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846972B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-a6235f614ee44d2c907dd479bd36507d
Source note	uspto-grants-2014_09