Acetic Acid → HCID 131725317, compound

Participants

Reaction Steps

To a solution of p-nitrobenzyl (1R,5S,6S)-2-(1-{4-[(1S)-2-(t-butyldimethylsilyloxy)-1-methyl-ethylcarbamoyl]-1,3-thiazol-2-yl}azetidin-3-yl)thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (940 mg, 1.28 mmol) (obtained as described in Example 40(1)) in tetrahydrofuran (47 ml) were added acetic acid (221 μl, 3.85 mmol) and a solution of 1 M tetrabutylammonium fluoride in tetrahydrofuran (3.85 ml, 3.85 mmol) in an ice bath and the mixture was stirred for 3 days at room temperature. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was 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 using ethyl acetate: methanol (99:1 and 9:1) as the eluant to afford p-nitrobenzyl (1R,5S,6S)-2-{1-[4-((1S)-2-hydroxy-1-methylethylcarbamoyl)-1,3-thiazol-2-yl]azetidin-3-yl}thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (462 mg, yield 58%) as a pale yellow solid.

Provenance & Evidence