Реакция #5213

ord-af6090bbcc8144a0a01582239a197438

Уравнение реакции

COS(=O)(=O)F
methyl fluorosulfonate
COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CCN3C2)cc1
(6S, 8S)-8-(4-methoxybenzylthio)-4-methyl-5-oxo-1,4-diazabicyclo-[4.3.0]nonane
→
COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CC[N+]3(C)C2)cc1.O=S(=O)([O-])F
title compound
COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CC[N+]3(C)C2)cc1.O=S(=O)([O-])F
(6S, 8S)-1,4-Dimethyl-8-(4-methoxybenzylthio)-5-oxo-4-aza-1-azoniabicyclo[4.3.0]nonane fluorosulfonate

Реактанты

COS(=O)(=O)F
methyl fluorosulfonate
COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CCN3C2)cc1
(6S, 8S)-8-(4-methoxybenzylthio)-4-methyl-5-oxo-1,4-diazabicyclo-[4.3.0]nonane

Реагенты

Нет

Растворители

CCOCC
diethyl ether
ClCCl
methylene chloride

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Фильтрацияthe resulting crystals were collected by filtration
  2. 2
    Другоеdried under reduced pressure

Методика

461 μl of methyl fluorosulfonate was added, whilst ice-cooling, to a solution of 1.71 g of (6S, 8S)-8-(4-methoxybenzylthio)-4-methyl-5-oxo-1,4-diazabicyclo-[4.3.0]nonane dissolved in 60 ml of methylene chloride, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the mixture was diluted with diethyl ether, and the resulting crystals were collected by filtration and dried under reduced pressure, to afford 2.09 g of the title compound as colorless crystals, melting at 208°-210° C.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05242914uspto-grants-1993_09