Acetic Acid → HCID 131725324, compound

Participants

Reaction Steps

p-Nitrobenzyl (1R,5S,6S)-2-(1-{4-[(1S,2S)-1-(t-butyldimethylsilyloxymethyl)-2-methyl-butylcarbamoyl]-1,3-thiazol-2-yl}azetidin-3-yl)thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (760 mg, 0.982 mmol) (obtained as described in Example 43(1)) in tetrahydrofuran (38ml) was added to acetic acid (169 μl, 2.95 mmol) and 1 M tetrabutylammonium fluoride in tetrahydrofuran solution (2.95 ml, 2.95 mmol) and the mixture was stirred at room temperature for 3 days. After checking the completion of the reaction, ethyl acetate and water were added to the reaction mixture. The resulting mixture was shaken in a separatory funnel and the ethyl acetate layer was separated, washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluant: ethyl acetate→ethyl acetate: methanol (9:1)) to afford p-nitrobenzyl (1R,5S,6S)-2-{1-[4-((1S,2S)-1-hydroxymethyl-2-methylbutylcarbamoyl)-1,3-thiazol-2-yl]azetidin-3-yl}thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (390 mg, yield 60%) as a pale yellow solid.

Provenance & Evidence