1,2-Dichloroethane → HCID 59714664, compound

Participants

Reaction Steps

A mixture of 2-amino-cyclohex-1-enecarboxylic acid (4-ethoxy-phenyl)-amide (1.46 g, 5.60 mmol), N-Boc-D-alanine (1.06 g, 5.60 mmol), EDC (1.60 g, 8.4 mmol), HOBT (151 mg, 1.12 mmol) and 1.0 mL of N-methylmorpholine in 30 mL of methylene chloride was allowed to stir at room temperature for 28 h. Upon completion, the mixture was concentrated and 30 mL of saturated aqueous sodium bicarbonate was added. The resulting mixture was extracted with ethyl acetate (30 mL×3). The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The material was purified by chromatography on a silica gel column using 30% ethyl acetate/hexane successively as the eluents to give 1.53 g of product H4. 1H NMR (400 MHz, CDCl3) δ: 12.95 (s, 1H), 7.36 (d, J=8.86 Hz, 2H), 7.25 (br s, 1H), 8.87 (d, J=8.95 Hz, 2H), 5.23 (br s, 1H), 4.13 (br s, 1H), 4.02 (q, J=7.0 Hz, 2H), 3.01 (br s, 2H), 2.37 (br s, 2H), 1.70 (m, 4H), 1.43 (s, 9H), 1.41 (dd, J=7.0, 7.0 Hz, 3H), 1.40 (obscured d, J=7.07 Hz, 3H). MS (ESI+) 432 [M+H]+.

Provenance & Evidence