Reaktion #2010809

ord-eae58809b42c45d583c6015e2393d7bd

Reaktionsgleichung

CCCCc1noc(C)c1/C=C/c1nc(C)c(C(=O)O)s1
2-[(E)-2-(3-butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid
Cl.N[C@@H]1CCC[C@H]1O
trans-(−)-2-aminocyclopentanol hydrochloride
CCCCc1noc(C)c1/C=C/c1nc(C)c(C(=O)N[C@@H]2CCC[C@H]2O)s1
title compound
Ausbeute 75.0%
CCCCc1noc(C)c1/C=C/c1nc(C)c(C(=O)N[C@@H]2CCC[C@H]2O)s1
2-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid ((1R,2R)-2-hydroxy-cyclopentyl)-amide
Ausbeute 75.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

As described for example 104, 2-[(E)-2-(3-butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid (153 mg, 0.5 mmol) was converted, using trans-(−)-2-aminocyclopentanol hydrochloride instead of rac-2-amino-1-butanol, to the title compound (146 mg, 75%) which was obtained as an off white solid after purification by chromatography (silica, 50 to 100% ethyl acetate in heptane) and recrystallization from ethyl acetate/heptane. MS: m/e=390.3 [M+H]+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08178522B2uspto-grants-2012_05