Reaction #2275729

Reaction equation

3-Amino-azetidine-1-carboxylic acid tert-butyl ester

(3-trifluoromethyl-benzoylamino)-acetic acid

EDCI

HOBT

→

title compound

3-[2-(3-Trifluoromethyl-benzoylamino)-acetylamino]azetidine-1-carboxylic acid tert-butyl ester

Solvents

DCM

Conditions

Workup

1. 1
   OtherThe reaction solution was partitioned between DCM and water
2. 2
   WashThe organic layer was washed with brine
3. 3
   Dryingdried over anhydrous Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   Otherto give a yellow oil
7. 7
   Otherpurified by silica gel column on a CombiFlash® system

Procedure

3-Amino-azetidine-1-carboxylic acid tert-butyl ester (AstaTech, 1.2 g, 6.97 mmol) and (3-trifluoromethyl-benzoylamino)-acetic acid (Bionet Building Blocks, 1.57 g, 6.36 mmol) were treated with EDCI (Aldrich, 1.57 g, 6.36 mmol), HOBT (Aldrich, 1.22 g, 6.36 mmol) in DCM (10 mL) at room temperature for 4 hours. The reaction solution was partitioned between DCM and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a yellow oil, and purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid.

Source