Ethyl chloroformate → HCID 86766931, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from example 76 (100 mg, 0.2 mmol) in THF (3 mL) at −78° C. was added NaHMDS (181 μL, 0.2 mmol) and the mixture was stirred at −78° C. for 15 min. Ethyl carbonochloridate (86 μL, 0.9 mmol) was added at −78° C. and the mixture was allowed to warm up to rt and stirred for 1 h. The reaction mixture was quenched with a saturated aqueous NH4Cl solution, then was diluted in EtOAc and extracted with brine. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by preparative HPLC (Column: Sunfire C18, 30×100 mm, 5 μm. Flow: 30 mL/min. Gradient 5-100% B in 20 min; A=0.1% TFA in water, B═CH3CN). tR: 1.39 min (LC-MS 2); ESI-MS: 624.4/626.4 [M+H]+ (LC-MS 2).

Provenance & Evidence