Trifluoroacetic acid → HCID 10270779, compound

Participants

Reaction Steps

To a solution of N-(2-(N-(N-carbo-tert-butoxyglycyl)aminomethyl)-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.050 g, 0.105 mmol) in CH2Cl2 (3 mL) at room temp. was added trifluoroacetic acid (0.50 mL, 6.49 mmol, 62 equiv). The resulting mixture was stirred for 3 h, washed with a saturated NaHCO3 solution, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (for CH2Cl2 to 20% MeOH/CH2Cl2) to give N-(2-(N-glycylaminomethyl)-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.019 g, 48%): mp 93-6° C.; 1H NMR (CDCl3) δ1.14 (s, 9H), 2.08 (s, 3H), 3.89 (s, 2H), 4.34 (br s, 7H), 6.67 (s, 1H), 6.87 (d, J=8.1 Hz, 2H), 7.12 (d, J=8.5 Hz, 2H), 7.3 (m, 2H).

Provenance & Evidence