Reacción #5161

ord-50ea5bd8d6b3424b8c861a6db968fd72

Ecuación de reacción

CC1C(SC2CNC(=O)C2)=C(C(=O)[O-])N2C(=O)C([C@@H](C)O)[C@@H]12.[Na+]
sodium 2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
Cc1oc(=O)oc1CBr
5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide
→
Cc1oc(=O)oc1COC(=O)C1=C(SC2CNC(=O)C2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12
title compound
Rendimiento 79.5%
Cc1oc(=O)oc1COC(=O)C1=C(SC2CNC(=O)C2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12
5-Methyl-2-oxo-1,3-dioxolen-4-ylmethyl (1R, 5S, 6S)-2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
Rendimiento 79.5%

Reactantes

CC1C(SC2CNC(=O)C2)=C(C(=O)[O-])N2C(=O)C([C@@H](C)O)[C@@H]12.[Na+]
sodium 2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
Cc1oc(=O)oc1CBr
5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

Following a procedure similar to that described in Example 39, but using 50 mg of sodium 2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate and 55 mg of 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide, 50 mg of the title compound were obtained as a colorless powder.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05242914uspto-grants-1993_09