Triethylamine → Methyl 5-(tert-butoxycarbonylamino)-4-(2-methoxy-2-oxoethylamino)thiophene-2-carboxylate

Participants

Reaction Steps

To a solution of methyl 4-amino-5-(tert-butoxycarbonylamino)thiophene-2-carboxylate 89 (0.037 mmol, 10 mg) in CH2Cl2 (1 mL), triethylamine (0.367 mmol, 51.2 μL) and methyl bromoacetate (0.184 mmol, 17.45 μL) were added and stirred at rt for 3 h. The reaction was quenched in water and extracted with CH2Cl2. The organic layer was dried with phaseseparator whereafter and concentrated under reduced pressure to give methyl 5-(tert-butoxycarbonylamino)-4-(2-methoxy-2-oxoethylamino)thiophene-2-carboxylate 90 (10 mg, 79%). NMR (400 MHz, CDCl3) 1.54 (s, 9H), 3.31 (br s, 1H), 3.77 (s, 3H), 3.79 (d, J=6.3 Hz, 2H), 3.82 (s, 3H), 7.38 (s, 1H), 7.54 (br s, 1H). (m/z)=345 (M+H)+.

Provenance & Evidence