Triethylamine → [1-(4-Carbamoyl-oxazol-2-yl)-cyclopropyl]-carbamic acid benzyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Ammonium Bicarbonate	HCID 14013	—
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-(1-Benzyloxycarbonylamino-cyclopropyl)-oxazole-4-carboxylic acid	HCID 58431151	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[1-(4-Carbamoyl-oxazol-2-yl)-cyclopropyl]-carbamic acid benzyl ester	HCID 58431031	83.3%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a solution of 2-(1-benzyloxycarbonylamino-cyclopropyl)-oxazole-4-carboxylic acid (0.20 g, 0.66 mmol) in DMF (3 mL) was added HATU (0.25 g, 0.66 mmol) and Et3N (0.16 g, 2.0 mmol). Ammonium hydrogen carbonate was then added and the reaction vessel sealed. The mixture was heated at 60° C. for 18 h. The reaction was allowed to cool to room temperature and diluted with water. The mixture was extracted with EtOAc (3×100 mL) and the combined extracts were washed with water, brine and dried with MgSO4. The mixture was filtered and concentrated to give [1-(4-carbamoyl-oxazol-2-yl)-cyclopropyl]-carbamic acid benzyl ester (0.17 g, 0.55 mmol).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08552205B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-ac6b32f5d4d64647a0dc58f28d4735ca
Source note	uspto-grants-2013_10