Hydroxyamine hydrochloride → HCID 71073681, compound

Participants

Reaction Steps

As reported for the synthesis of 19b in reference 46, benzhydrylidene aza-propargylglycinyl-proline tert-butyl ester 18a (100 mg, 0.23 mmol) was stirred with hydroxylamine hydrochloride (29 mg, 0.42 mmol) in 20 mL of pyridine overnight at 60° C. The volatiles were removed by rotary evaporation followed by co-evaporation with dichloromethane and ethyl acetate until solidification. Purification by flash chromatography on silica gel using a 1:1 mixture of ethyl acetate in hexane afforded amine 19a (51.3 mg, 84%) as a pale yellow foam: Rf=0.39 (hexane/EtOAc 1:1); [α]20D −48° (c 1.15, CHCl3). 1H NMR (CDCl3, 400 MHz) δ 1.46 (s, 9H), 1.84-1.99 (m, 3H), 2.13-2.20 (m, 1H), 2.31 (s, 1H), 3.64 (m, 2H), 4.16 (d, J=17.2 Hz, 1H), 4.24 (d, J=17.2 Hz, 1H), 4.43 (m, 1H); 13C NMR (CDCl3, 100 MHz) δ23.3, 27.6, 30.1, 42.6, 48.8, 61.5, 73.0, 78.1, 80.3, 159.8, 172.5. HRMS m/z calculated for C13H21N3O3 Na [M+Na]+ 290.1475. found 290.1488.

Provenance & Evidence