Synthesis of (S)-3-heteroaryl-2-hydroxy-l-propyl benzoates by ‘ring switching’ methodology

✍ Scribed by Damjana Mihelič; Renata Jakše; Jurij Svete; Branko Stanovnik; Simona GoliČ Grdadolnik

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2001
• Tongue: English
• Weight: 88 KB
• Volume: 38
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570380610

✦ Synopsis

Abstract

(S)‐5‐Benzoyloxymethyl‐3‐[(E)‐(dimethylamino)methylidene]tetrahydrofuran‐2‐one (6), prepared in 5 steps from L‐glutamic acid (1), was used as precursor in a one step ‘ring switching’ synthesis of (S)‐2‐hydroxy‐3‐heteroaryl‐l‐propyl benzoates 13‐18, 23, 24. In the reaction of 6 with 2‐aminopyridine (21) and 2‐amino‐4,6‐dimethylpyrimidine (22) the corresponding dimethylamine substitution products (25, 26) were obtained.