Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 362099Generated: October 30, 2026

p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → (1R,5S,6S)-2-[(2S,4S)-2-(Azetidin-3-ylcarbamoyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid

https://huagongshe.com/reaction/362099

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylateHCID 15871605—
Reactant(2S,4S)-4-mercapto-2-[1-(4-nitrobenzyloxycarbonyl)azetin-3-ylaminocarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidineHCID 131721113—
Product(1R,5S,6S)-2-[(2S,4S)-2-(Azetidin-3-ylcarbamoyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acidHCID 2294184314.7%

Reaction Steps

Following a procedure similar to that described in Example 121(1), followed by a procedure similar to that described in Example 49, but using 0.80 g of 4-nitrobenzyl (1R,5R,6S)-2-(diphenylphosphoryloxy)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (prepared as described in Preparation 123) and 0.95 g of (2S,4S)-4-mercapto-2-[1-(4-nitrobenzyloxycarbonyl)azetin-3-ylaminocarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (prepared as described in Preparation 33), 86 mg of the title compound was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05866564
Source datasetuspto-grants-1999_02
ORD IDord-1942276a28ff47e8a00f085ede5f5940
Source noteuspto-grants-1999_02