Reaktion #1488965

ord-d0bb4ecfde2e45f392a80def9e93de22

Reaktionsgleichung

CC1(C)CCC(C)(C)c2cc(-c3csc(C4CCNCC4)n3)ccc21.Cl
4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrochloride
C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O
N-(tert-butoxycarbonyl)-L-threonine
Cl
HCl
→
C[C@@H](O)[C@H](N)C(=O)N1CCC(c2nc(-c3ccc4c(c3)C(C)(C)CCC4(C)C)cs2)CC1
(2S,3R)-2-amino-3-hydroxy-1-{4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-1-yl}butan-1-one

Edukte

CC1(C)CCC(C)(C)c2cc(-c3csc(C4CCNCC4)n3)ccc21.Cl
4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrochloride
C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O
N-(tert-butoxycarbonyl)-L-threonine
Cl
HCl

Reagenzien

Keine

Lösungsmittel

C1COCCO1
dioxane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe product was purified by means of preparative HPLC

Vorschrift

The preparation was carried out analogously starting from 200 mg (0.47 mmol) of 4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrochloride and 113 mg (0.52 mmol) of N-(tert-butoxycarbonyl)-L-threonine. The protecting group was cleaved off as already described using HCl in dioxane. The product was purified by means of preparative HPLC and is in the form of the hydrochloride.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08907098B2uspto-grants-2014_12