Diketene → HCID 57609712, compound

Participants

Reaction Steps

Prepared according to the representative procedure (Method B) using (4-methoxy-benzylamino)-acetic acid benzyl ester (910 mg, 3.19 mmol), 2-hydroxypyridine (304 mg, 3.20 mmol) in THF (25 mL), and ketene dimer (1.0 mL, 16 mmol). Purification by flash chromatography on SiO2 (1:4 EtOAc/hexanes) gave keto ester 54e (930 mg, 78%) as a colorless oil. Due to the presence of enol tautomers and amide rotamers, the NMR spectra of this compound is extremely complex and so line listing is not provided. Rf=0.28 (33% EtOAc/hexanes); IR (neat) 1747, 1720, 1646 cm−1; LRMS (ESI) Calcd. for C21H23NO5 [M+H] 370, found 370; HRMS (ESI) Calcd. for C21H23NO5 [M+H] 370.1654, found 370.1655.

Provenance & Evidence