Reaktion #48309

ord-e39700be6b544b94bf846525f97b1aab

Reaktionsgleichung

COC(=O)[C@@H](CI)C(=O)OC(C)(C)C
(R)-methyl 2-(tert-butoxycarbonyl)-3-iodopropanoate
CC(C)[Si](c1ncc(Br)s1)(C(C)C)C(C)C
5-bromo-2-(triisopropylsilyl)thiazole
→
COC(=O)[C@H](Cc1cnc([Si](C(C)C)(C(C)C)C(C)C)s1)C(=O)OC(C)(C)C
title compound
COC(=O)[C@H](Cc1cnc([Si](C(C)C)(C(C)C)C(C)C)s1)C(=O)OC(C)(C)C
(S)-methyl 2-(tert-butoxycarbonyl)-3-(2-(triisopropylsilyl)thiazol-5-yl)propanoate

Edukte

COC(=O)[C@@H](CI)C(=O)OC(C)(C)C
(R)-methyl 2-(tert-butoxycarbonyl)-3-iodopropanoate
CC(C)[Si](c1ncc(Br)s1)(C(C)C)C(C)C
5-bromo-2-(triisopropylsilyl)thiazole
—
Thiazoles

Reagenzien

Keine

Lösungsmittel

—
Halogen

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeprepared
  2. 2
    SonstigeApplication to the Total Synthesis of WS75624 B, Journal of Organic Chemistry (2004)

Vorschrift

The title compound was synthesized in a manner analogous to that described Example 475, using (R)-methyl 2-(tert-butoxycarbonyl)-3-iodopropanoate and 5-bromo-2-(triisopropylsilyl)thiazole (prepared according to Stangeland, Eric L.; Sammakia, Tarek, Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624 B, Journal of Organic Chemistry (2004), 69(7), 2381-2385.). MS m/z: 443.3 (100%, M+1).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745484B2uspto-grants-2010_06