Ethyl (chloroformyl)acetate → HCID 57906588, compound

Participants

Reaction Steps

A solution of (2-amino-5-bromo-pyridin-4-ylmethyl)-carbamic acid tert-butyl ester (3.5 g, 11.6 mmol, prepared according to Example 1, Step 1.3) and freshly prepared 2-chloro-3-oxo-propionic acid ethyl ester (8.97 g, 59.6 mmol, prepared according to a patented procedure U.S. Pat. No. 5,559,158-A1) in dioxane (60 mL) was stirred at RT for 14 h. The reaction mixture was diluted in AcOEt (400 mL) and washed with a 2.0 M aqueous Na2CO3 solution (2×200 mL). The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→2:8) to yield the title compound (1.31 g, 4.83 mmol, 41%) as a light yellow solid. MS: 398 [M+1]+; HPLC: AtRet=1.85; TLC: RF 0.47 (hexane/DCM/TBME 1:1:2).

Provenance & Evidence