Diisopropylethylamine → HCID 140484921, compound

Participants

Reaction Steps

The acid (43 mg, 0.116 mmol) obtained from Step D was placed in a flask with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester (32 mg, 0.128 mmol), PyAOP (76 mg, 0.145 mmol) and dissolved in 2 mL DMF. DIEA (61 μL, 0.348 mmol) was added and the reaction allowed to stir for 2 h. The reaction was diluted with EtOAc and 5% NaHCO3 was added and stirred for 10 min. The phases were separated and the aqueous phase extracted 2× with EtOAc, dried with sodium sulfate and concentrated. Purified by HPLC and lyopholized to give the product as a white solid (34 mg, 41% yield). 1HNMR (300 MHz, CDCl3) δ 1.614 (s, 9H) 2.3 (m, 1H) 2.5 (s, 3H) 2.6 (m, 1H) 3.4–3.6 (m, 2H) 3.6–3.8 (m, 2H) 5.2 (m, 1H) 5.25 (s, 2H) 7.4 (m, 9H) 7.6 (m, 2H) 7.8 (m, 2H).

Provenance & Evidence