Triethylamine → HCID 13676801, compound

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Ammonium Bicarbonate	HCID 14013	—
Reactant	1-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic acid	HCID 3589012	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 13676801	HCID 13676801	82.2%

Reaction Steps

To a solution of 1-benzyloxycarbonylamino-cyclopropanecarboxylic acid (7.0 g, 29.8 mmol) in DMF (30 mL) was added HATU (11.3 g, 29.8 mmol) and Et3N (4.3 mL, 29.8 mmol). The mixture was allowed to stir at room temperature for 20 min, then ammonium hydrogen carbonate (7.06 g, 89.3 mmol) was added in one portion. The reaction was heated at 60° C. for 12 h. The mixture was cooled to room temperature, diluted with water and extracted with EtOAc (2×100 mL). The combined extracts were washed with satd NaHCO3, water, brine and dried with MgSO4. The mixture was filtered and the solvent removed to give (1-carbamoyl-cyclopropyl)-carbamic acid benzyl ester (5.5 g, 24.5 mmol) as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08552205B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-5a224b1755f7468285e3e3397fedb68c
Source note	uspto-grants-2013_10