4-Methylmorpholine → N-(2-((tert-butyldimethylsilyloxy)methyl)-4-methoxyphenyl)-3,3,3-trifluoropropanamide

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	3,3,3-Trifluoropropionic acid	HCID 2777972	—
Reactant	2-((Tert-butyldimethylsilyloxy)methyl)-4-methoxyaniline	HCID 66980081	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(2-((tert-butyldimethylsilyloxy)methyl)-4-methoxyphenyl)-3,3,3-trifluoropropanamide	HCID 66980120	—

Reaction Conditions

Temperature	20 °C

Reaction Steps

A mixture of 2-((tert-butyldimethylsilyloxy)methyl)-4-methoxyaniline (14.0 g), 3,3,3-trifluoro-propionic acid (7.30 g, 57.0 mmol), EDCI (15.0 g, 76.5 mmol), HOBT (11.0 g, 80.2 mmol) and NMM (22 mL, 157 mmol) in anhydrous CH2Cl2 (200 mL) was stirred at 20° C. for 2 hours. The mixture was diluted with CH2Cl2 (100 mL), the organic layer was washed with 1M HCl (100 mL), H2O (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated to give the product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09139528B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-ecfd195c4cef4aa585ce04c85ed63463
Source note	uspto-grants-2015_09