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Non-hazardous synthesis of isocephosphorin intermediates via α-vinylamino-β-lactams

✍ Scribed by Ajay K Bose; Maghar S Manhas; Shanti G Amin; Jagdish C Kapur; J Kreder; L Mukkavilli; Bhagat Ram; John E Vincent

Book ID
104237837
Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
249 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reaction of a Schiff Bose derived from verotrylamine and cinnamaldehyde with (a-methyl-P-olkoxycarbonyl)-vinylamino acetic acid (from glycine and on ocetoocetate ester) in presence of a chloroformate ester and triethylomine constitutes a safe synthesis of a-vinylamino p-loctoms that con be converted by literature methods to known intermediates for the synthesis of /socephalosporlns and analogs.

The reaction of P-dicarbonyl compounds with a-amino acids and alkali leads to aminoprotected amino acids or "Dane Salts" (2) which have been used for the preparation of peptides(2) and for the acylation of 6-APA to ampicillin(3) and II-ADCA to cephradlne(4)

📜 SIMILAR VOLUMES

Asymmetric synthesis of α-hydroxy acids
Asymmetric synthesis of α-hydroxy acids via β-Lactams
✍ V. Srirajan; A.R.A.S. Deshmukh; V.G. Puranik; B.M. Bhawal 📂 Article 📅 1996 🏛 Elsevier Science 🌐 English ⚖ 356 KB

A diastereoselective synthesis of [5-Lactams 5a-e and 6a-e has been achieved, via a Staudinger reaction using imines derived from (1S)-(+)-camphor-10-sulfonamide, in good yields. The major diastereomers 6a-e were isolated in pure form by crystallization. The absolute configuration of the [5-1actam 6