Hydrochloric Acid → 2,2,2-Trichloroethyl 2-(3-iodo-4-nitrobenzamido)acetate

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Reaction Steps

To a stirred solution 2,2,2-trichloroethyl N-Boc glycinate (1.25 g, 4.08 mmol) in DCM (10 mL) was added HCl in dioxane (2N, 10 mL) and stirred at rt for 2 h. Solvents were removed under reduced pressure, and was dissolved in DCM (10 mL) and added triethylamine (1.48 mL, 10.23 mmol) at 0° C. A solution of 3-iodo-4-nitrobenzoyl chloride (prepared from 3-iodo-4-nitrobenzoic acid, 1 g and SOCl2, 10 mL) in DCM (10 mL) was added to the above reaction mixture at 0° C. Then the reaction mixture was stirred at rt for 3 h and worked-up as described in intermediate 1 to obtain the product as a cream color solid (1.28 g, 78%), mp 98-100° C. 1H NMR (400 MHz, CDCl3): δ 8.46 (1H, s), 7.90 (2H, s), 6.67 (1H, br s), 4.86 (2H, s), 4.23 (2H, d, J=5.2 Hz); LC-MS (negative ion mode): m/z 479 (M−H)−.

Provenance & Evidence