HCID 178448367, compound → HCID 178448366, compound

Participants

Reaction Steps

To the compound 97 (1.74 g) in an acetic acid (35 ml) suspension, zinc powder (3.5 g) was added, and the mixture was stirred at room temperature for 4 hours. The insolubles were filtered out and the filtrate was concentrated in vacuo. To the residue, acetic acid (20 ml) was added, the mixture was stirred at 60° C. for 1 hour, then the insolubles were filtered out. The filtrate was concentrated in vacuo, the residue was diluted with chloroform-methanol-acetic acid (5:1:0.1) (20 ml), and tha mixture was stirred at room temperature for 1 hour. The insolubles were collected by filtration, then ethyl acetate (105 ml), saturated aqueous ammonium chloride solution (105 ml), and water (53 ml) were added to the obtained crystals, and the mixture was stirred at room temperature for 4 hours. The layers were separated, and the aqueous layer was extracted with ethyl acetate (50 ml×2). The organic layer and the extract were combined, then the mixture was washed with brine, dried over sodium sulfate, then concentrated. The residue was purified by flash column chromatography (silica gel, chloroform/ethyl acetate/methanol=50/50/5 to 50/50/10) to obtain 2-amino-4-[(1R)-1-({[(6S)-6-(5-chloro-2-methoxybenzyl)-3-(hydroxyimino)-7-oxo-1,4-diazepan-1-yl]carbonyl}amino)butyl]benzoic acid (compound 14) (1.07 g).

Provenance & Evidence