2,2,2-Trichloroethyl chloroformate → HCID 86691454, compound

Participants

Reaction Conditions

Reaction Steps

The product of Step 2 (38 g) was dissolved in toluene (400 mL). To this, 2,2,2-trichloroethyl chloroformate (90 mL) was added. The reaction mixture was heated to reflux under Argon purging for 3 hr. The reaction mixture was allowed to cool to 25° C. and concentrated under vacuum to give ˜200 g crude material. Purification was performed as follows on the BIOTAGE® AB ISOLERA™ flash chromatography system. Crude product (50 g) was loaded on a SNAP cartridge containing 340 g silica gel and eluted using a gradient of acetone and hexane. Fractions containing product were pooled and evaporated under vacuum. Yield of purified product (combined runs): 42 g. 1H NMR (CDCl3): 1.2 δ (3H, —CH—CH3 of isopropyl), 2.8 δ (6H, —N—(CH3)), 2.5, 2.6, 3.1 δ (1H, 1H, 1H —CH2-CH—CH3 of isopropyl), 3.8 δ (3H, —OCH3), 6.8-7.5 δ (9H, phenyl rings). Mass spectrometry: m/z=469 (M+H), 486 (M+H2O)

Provenance & Evidence