Reaktion #2254197

Reaktionsgleichung

Compound ( 15a )

(S)-(9H-Fluoren-9-yl)methyl (5-(3-(tert-butoxy)-2-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)guanidino)-1-oxo-1-(4-(5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenylsulfonamido)pentan-2-yl)carbamate

piperidine

→

title compound

(S)-2-Amino-5-(2-hydroxyguanidino)-N-((4-(5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)sulfonyl)pentanamide

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto remove the Fmoc protecting group
2. 2
   SonstigeThe residue is purified by reverse phase chromatography (acetonitrile/water with 0.05% trifluoroacetic acid)
3. 3
   workup.DISSOLUTIONdissolved in 95% trifluoroacetic acid-methylene chloride (0.1 M)
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe residue is purified by reverse phase chromatography (acetonitrile/water with 0.05% trifluoroacetic acid)

Vorschrift

Compound (15a) is treated with 20-50% piperidine in N,N-dimethylformamide (0.1 M) to remove the Fmoc protecting group. The residue is purified by reverse phase chromatography (acetonitrile/water with 0.05% trifluoroacetic acid) and then dissolved in 95% trifluoroacetic acid-methylene chloride (0.1 M). The mixture is stirred at 25° C. for 6 h and then concentrated under reduced pressure. The residue is purified by reverse phase chromatography (acetonitrile/water with 0.05% trifluoroacetic acid) to provide the title compound.

Quelle