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tert-butyl {3-[([cyclopropyl(imino)methyl]amino}oxy)carbonyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1.28 g
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 16.0h;Inert atmosphere;
2-tert-Butoxycarbonylamino-4,5,6,7-tetrahydro-benzo[]thiophene-3-carboxylic acid (1 g; prepared according to Y. Huang et al, Chem. Biol. Drug Des. 2010, 76, 116-129) was dissolved in DMF (33.6 mL) at RT under argon. Then HATU (1.29 g), DIPEA (443 mg) and (Z)-N*- hydro xycyclopropanecarboximidamide (374 mg) were added and the reaction solution was stirred at RT for 16 h until TLC (n-heptane/EtOAc: 1/lv/v) indicated completion of the reaction. The reaction mixture was diluted with H20 and extracted with EtOAc. The combined organic layers were washed with 2M KHCO3, dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/n-heptane, gradient from 0 to 25%) to give the desired compound as a light yellow solid (1.28 g). MS (ESI): m/z = 380.1 [M+H] +.
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