Reaktion #1183467

Reaktionsgleichung

N-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-N-(2,2-dimethoxy-ethyl)-2-(3-iodo-phenylamino)-propionamide

2-(3-iodo-phenylamino)-propionic acid

intermediate 23

2-(3-iodo-phenylamino)-propionic acid

1-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-4-(3-iodo-phenyl)-3-methyl-piperazin-2-one

{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-(2,2-dimethoxy-ethyl)-amine

→

title compound

1-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-4-(3-iodo-phenyl)-3-methyl-piperazin-2-one

Reaktionsbedingungen

Vorschrift

The title compound was produced in analogy with examples 87/88, steps A-C. Thus, 2-(3-iodo-phenylamino)-propionic acid (intermediate 23) was coupled with {3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-(2,2-dimethoxy-ethyl)-amine (example 83C) in step A, leading to N-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-N-(2,2-dimethoxy-ethyl)-2-(3-iodo-phenylamino)-propionamide. This was cyclized to 1-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-4-(3-iodo-phenyl)-3-methyl-piperazin-2-one in step B. Finally, deprotection in step C afforded the title compound. Light yellow gum, MS: 484.3 (M+H)+)

Quelle