3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → HCID 86727484, compound

Participants

Reaction Steps

A solution of 6-amino-7-benzyloxy-4-methyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.065 g, 0.19 mmol) and tert-butyl 3-oxoazetidine-1-carboxylate (0.061 g, 0.36 mmol) in MeOH (10 mL) and AcOH (1 mL) was heated at 70° C. for 14 h. The reaction mixture was cooled to ambient temperature and sodium cyanoborohydride (0.022 g, 0.36 mmol) was added. The reaction mixture was heated at 70° C. for 1 hr then cooled to ambient temperature. The solvent was removed in vacuo and the residue was purified by preparative TLC (eluting with 50% EtOAc in petroleum ether) to give 3-(7-benzyloxy-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (0.028 g, 32%). LC/MS (Table 1, Method 2) Rt=1.205 min; MS m/z: 516 [M+23]+

Provenance & Evidence