Reaktion #975419

ord-a1ca55a43ef64dd7b7dd92878deb7d9a

Reaktionsgleichung

CCCC1CCNCC1
4-propylpiperidine
COc1ccc(CCC[C@@H](C(=O)O)[C@@H]2OC(C)(C)OC2=O)cc1
(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-(4-methoxyphenyl)pentanoic acid
CC(C)C[C@H](C(=O)N1CCN(c2nc(-c3ccccc3)ns2)CC1)[C@H](O)C(=O)NO
Intermediate 2
CC(C)C[C@H](C(=O)N1CCN(c2nc(-c3ccccc3)ns2)CC1)[C@H](O)C(=O)NO
(2S,3S)-N,2-dihydroxy-5-methyl-3-{[4-(3-phenyl-1,2,4-thiadiazol-5-yl)-1-piperazinyl]carbonyl}hexanamide
COc1ccc(Br)cc1
4-bromoanisole
→
CCCC1CCN(C(=O)[C@H](CCCc2ccc(OC)cc2)[C@H](O)C(=O)NO)CC1
title product
CCCC1CCN(C(=O)[C@H](CCCc2ccc(OC)cc2)[C@H](O)C(=O)NO)CC1
(2S,3R)—N,2-dihydroxy-6-(4-methoxyphenyl)-3-[(4-propylpiperidin-1-yl)carbonyl]hexanamide

Edukte

CCCC1CCNCC1
4-propylpiperidine
COc1ccc(CCC[C@@H](C(=O)O)[C@@H]2OC(C)(C)OC2=O)cc1
(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-(4-methoxyphenyl)pentanoic acid
CC(C)C[C@H](C(=O)N1CCN(c2nc(-c3ccccc3)ns2)CC1)[C@H](O)C(=O)NO
Intermediate 2
CC(C)C[C@H](C(=O)N1CCN(c2nc(-c3ccccc3)ns2)CC1)[C@H](O)C(=O)NO
(2S,3S)-N,2-dihydroxy-5-methyl-3-{[4-(3-phenyl-1,2,4-thiadiazol-5-yl)-1-piperazinyl]carbonyl}hexanamide
COc1ccc(Br)cc1
4-bromoanisole

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe title product was prepared
  2. 2
    Sonstigeprepared
  3. 3
    SonstigePurification by reverse-phase chromatography

Vorschrift

The title product was prepared following the procedure of Example 64 (step a and b) but starting from (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-(4-methoxyphenyl)pentanoic acid (prepared following the procedure of Intermediate 2 but using 4-bromoanisole in step b) and 4-propylpiperidine (Aldrich). Purification by reverse-phase chromatography gave the title product as a yellow powder. M−(ESI): 405.4; M+(ESI): 407.4. HPLC (Condition A): Rt: 3.6 min (HPLC purity: 94.9%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08247437B2uspto-grants-2012_08