HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate | HCID 15871605 | — |
| Reactant | (2S,4S)-4-mercapto-2-[1-(4-nitrobenzyloxycarbonyl)azetin-3-ylaminocarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine | HCID 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 acid | HCID 22941843 | 14.7% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05866564 |
| Source dataset | uspto-grants-1999_02 |
| ORD ID | ord-1942276a28ff47e8a00f085ede5f5940 |
| Source note | uspto-grants-1999_02 |