Triethylamine → [5-(4-Bromo-phenyl)-oxazol-4-yl]-carbamic acid (R)-1-phenyl-ethyl ester

https://huagongshe.com/reaction/919048

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	P,P-Diphenylphosphinic azide	HCID 199401	—
Reactant	1-Phenylethanol, (R)-	HCID 637516	—
Reactant	5-(4-Bromophenyl)oxazole-4-carboxylic acid	HCID 61637413	—
Solvent	Toluene	HCID 1140	—
Product	[5-(4-Bromo-phenyl)-oxazol-4-yl]-carbamic acid (R)-1-phenyl-ethyl ester	HCID 67963772	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

5-(4-Bromo-phenyl)-oxazole-4-carboxylic acid (0.5 g, 1.9 mmol), (R)-1-phenyl-ethanol (0.25 mL, 2.0 mmol) and triethylamine (0.55 mL, 3.8 mmol) were dissolved in toluene (10 mL). Diphenylphosphoryl azide (0.5 mL, 2.3 mmol) was added and the reaction was heated to 80° C. The reaction was monitored by analytical LCMS and when complete was cooled and submitted to standard aqueous workup. The crude material was purified on silica gel to provide the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09272990B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-35b3624a484f46eabe09acaf946b7d04
Source note	uspto-grants-2016_03