Triethylamine → tert-Butyl 3-(dimethylcarbamoyl)pentan-3-ylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Dimethylamine, hydrochloride	HCID 10473	—
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	2-(((Tert-butoxy)carbonyl)amino)-2-ethylbutanoic acid	HCID 15108504	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	tert-Butyl 3-(dimethylcarbamoyl)pentan-3-ylcarbamate	HCID 86674741	53.7%

Reaction Steps

2-(tert-butoxycarbonylamino)-2-ethylbutanoic acid ((200 mg, 0.87 mmol), HATU (CAN 148893-10-1, 660 mg, 1.74 mmol) and triethylamine (CAN 121-44-8, 260 mg, 2.61 mmol) was added to a solution of dimethylamine hydrochloride (CAN 506-59-2, 117 mg, 1.74 mmol) in DMF (10 mL). The mixture was stirred overnight at room temperature. The mixture was added to water (20 mL) and extracted with ethyl acetate (30 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate, concentrated, and purified by prep-HPLC (eluting with 30% ethyl acetate in petroleum ether) to give the product (120 mg, 53.7%); MS (EI): m/e=259.2 [M+H]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09290451B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-b508e1b93e154accaf61316c1fd42050
Source note	uspto-grants-2016_03