Triethylamine → [(1S,2R)-2-tert-butoxy-1-(1-pyrimidin-2-yl-cyclopropylcarbamoyl)-propyl]-carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	(2S,3R)-3-(tert-butoxy)-2-(((tert-butoxy)carbonyl)amino)butanoic acid	HCID 7015770	—
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	HCID 67390310	HCID 67390310	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[(1S,2R)-2-tert-butoxy-1-(1-pyrimidin-2-yl-cyclopropylcarbamoyl)-propyl]-carbamic acid tert-butyl ester	HCID 67390977	81.9%

Reaction Steps

To a solution of (2S,3R)-3-tert-butoxy-2-tert-butoxycarbonylamino-butyric acid (0.20 g, 0.72 mmol) in DMF (1 mL) was added HATU (0.27 g, 0.72 mmol), Et3N (0.30 mL, 2.2 mmol) and 1-pyrimidin-2-yl-cyclopropylamine dihydrochloride (0.15 g, 0.72 mmol.). The reaction was allowed to stir at RT for 24 h. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined extracts were washed with satd NaHCO3, 2N HCl, water and brine. The solution was dried with MgSO4, filtered and concentrated to give [(1S,2R)-2-tert-butoxy-1-(1-pyrimidin-2-yl-cyclopropylcarbamoyl)-propyl]-carbamic acid tert-butyl ester (0.23 g, 0.59 mmol).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08552205B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-7e498d787faf4d8093d492d2cfb64de0
Source note	uspto-grants-2013_10