Reaktion #71792

ord-93109e34f8a2498c9af758f82f8ac60e

Reaktionsgleichung

CO[C@@H]1CN(C(N)=S)CC[C@@H]1NC(=O)OCc1ccccc1
benzyl cis(±)-(1-carbamothioyl-3-methoxypiperidin-4-yl)-carbamate
CO[C@@H]1CN(C(N)=S)CC[C@@H]1NC(=O)OCc1ccccc1
Benzyl cis(±)-(1-carbamothioyl-3-methoxypiperidin-4-yl)-carbamate
CCOC(=O)CC(=O)CCl
ethyl 4-chloro-acetoacetate
→
CCOC(=O)Cc1csc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OC)C2)n1
title compound
Ausbeute 96.4%
CCOC(=O)Cc1csc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OC)C2)n1
Ethyl cis(±)-[2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazol-4-yl]acetate
Ausbeute 96.4%

Edukte

CO[C@@H]1CN(C(N)=S)CC[C@@H]1NC(=O)OCc1ccccc1
benzyl cis(±)-(1-carbamothioyl-3-methoxypiperidin-4-yl)-carbamate
CO[C@@H]1CN(C(N)=S)CC[C@@H]1NC(=O)OCc1ccccc1
Benzyl cis(±)-(1-carbamothioyl-3-methoxypiperidin-4-yl)-carbamate
CCOC(=O)CC(=O)CCl
ethyl 4-chloro-acetoacetate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The same operation as in Example (22b) was performed using benzyl cis(±)-(1-carbamothioyl-3-methoxypiperidin-4-yl)-carbamate obtained in Example (64b) (97 mg, 0.30 mmol) and ethyl 4-chloro-acetoacetate (60 μL, 0.44 mmol), to obtain 125.4 mg of the title compound as a colorless oily substance (96%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536197B2uspto-grants-2013_09