Réaction #5156

ord-c134e3f71f3f457ca6e219a28a76ce5e

Équation de réaction

C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12
4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate
CC[N+]1(C)C[C@@H](S)C[C@H]1C(=O)N(C)C
(2S, 4S)-2-(N,N-dimethylcarbamoyl)-1-ethyl-1-methyl-4-mercaptopyrrolidinium
→
CC[N+]1(C)C[C@@H](SC2=C(C(=O)[O-])N3C(=O)[C@H]([C@@H](C)O)[C@H]3C2)C[C@H]1C(=O)N(C)C
title compound
Rendement 10.1%
CC[N+]1(C)C[C@@H](SC2=C(C(=O)[O-])N3C(=O)[C@H]([C@@H](C)O)[C@H]3C2)C[C@H]1C(=O)N(C)C
(5R, 6S)-2-[(2S, 4S)-1-Ethyl-1-methyl-2-(N,N-dimethylcarbamoyl)pyrrolidinium-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate
Rendement 10.1%

Réactifs

C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12
4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate
CC[N+]1(C)C[C@@H](S)C[C@H]1C(=O)N(C)C
(2S, 4S)-2-(N,N-dimethylcarbamoyl)-1-ethyl-1-methyl-4-mercaptopyrrolidinium

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

Following a procedure similar to that described in Example 6, but using 459 mg of 4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate and 580 mg of the crude (2S, 4S)-2-(N,N-dimethylcarbamoyl)-1-ethyl-1-methyl-4-mercaptopyrrolidinium salt [prepared as described in Example 9-(2)], 55 mg of the title compound were obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05242914uspto-grants-1993_09