Hydrochloric Acid → HCID 131718793, compound

Participants

Reaction Steps

(2R, 4S)-4-acetylthio-2-[(2S,4R)-2-hydroxymethyl-N-(p-nitrobenzyloxycarbonyl)pyrrolidin-4-ylmethyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine (150 mg, 0.24 mmol) was dissolved in a solution comprising methylene chloride (0.5 ml) and methanol (1.5 ml). A 2N sodium hydroxide aqueous solution (0.18 ml, 0.36 mmol) was dropwise added under cooling with ice in a nitrogen stream, and the reaction mixture solution was stirred for 20 minutes. After a 6N hydrochloric acid (0.06 ml, 0.36 mmol) was added to the reaction solution, the solution was poured into a saturated sodium chloride aqueous solution, then extracted with methylene chloride, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. By using the compound thus obtained and p-nitrobenzyl (1R, 5S, 6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (130 mg, 0.22 mmol), the same procedure as in Example 1-1) was carried out to obtain p-nitrobenzyl (1R, 5S, 6S)-6-[(R)-1-hydroxyethyl]-2-[(2R, 4S)-2-[(2S, 4R)-2-hydroxymethyl-N-(p-nitrobenzyloxycarbonyl)pyrrolidin-4-ylmethyl]pyrrolidin-4-ylthio]-1-methyl-1-carbapen-2-em-3-carboxylate (129 mg, yield: 58%).

Provenance & Evidence