Reaktion #74408

ord-a255db5d161c4ece86bb3aefa9bc2254

Reaktionsgleichung

CS(=O)(=O)OCCC1(CCOS(C)(=O)=O)SC(NC2CC3CCC2C3)=NC1=O
methanesulfonic acid 2-[2-(bicyclo[2.2.1]hept-2-ylamino)-5-(2-methanesulfonyloxy-ethyl)-4-oxo-4,5-dihydro-thiazol-5-yl]-ethyl ester
NC1CCCC1
cyclopentylamine
CO
MeOH
→
O=C1N=C(NC2CC3CCC2C3)SC12CCN(C1CCCC1)CC2
title compound
O=C1N=C(NC2CC3CCC2C3)SC12CCN(C1CCCC1)CC2
2-(Bicyclo[2.2.1]hept-2-ylamino)-8-cyclopentyl-1-thia-3,8-diaza-spiro[4.5]dec-2-en-4-one

Edukte

—
crude product
CS(=O)(=O)OCCC1(CCOS(C)(=O)=O)SC(NC2CC3CCC2C3)=NC1=O
methanesulfonic acid 2-[2-(bicyclo[2.2.1]hept-2-ylamino)-5-(2-methanesulfonyloxy-ethyl)-4-oxo-4,5-dihydro-thiazol-5-yl]-ethyl ester
NC1CCCC1
cyclopentylamine
CO
MeOH

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2
ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

A mixture of methanesulfonic acid 2-[2-(bicyclo[2.2.1]hept-2-ylamino)-5-(2-methanesulfonyloxy-ethyl)-4-oxo-4,5-dihydro-thiazol-5-yl]-ethyl ester (half of the crude product from above) and cyclopentylamine (799 mg, 9.38 mmol) in CH2Cl2 (1.5 mL) was stirred at room temperature for 4 d. Flash column chromatography (silica gel, 0-10% MeOH in CH2Cl2) afforded the title compound as an off-white solid (52 mg). MS (ESI, pos. ion) m/z: 348 (M+H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08541592B2uspto-grants-2013_09