Novel preparation of (2-azidomethyl)benzoic acid and an application as a protective group

Synthetic Communications

Volumn 32, Issue 21, 2002, Pages 3347-3355

  Matsuda, Hiroko ^a   Hashimoto, Masaru ^b   Okuno, Toshikatsu ^b  

^a IWATE UNIVERSITY   (Japan)

^b HIROSAKI UNIVERSITY   (Japan)

Author keywords

(2 Azidomethyl)benzoate; Hydroxyl protective group; Selective cleavage

Indexed keywords

(2 AZIDOMETHYL)BENZOIC ACID; BENZOIC ACID DERIVATIVE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; HYDROLYSIS; PURIFICATION; SYNTHESIS;

EID: 0036387081     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120014042     Document Type: Article

References (8)

1. Green, W.T.; Wuts, P.G.M. Protective Groups in Organic Synthesis, 3rd Ed.; John Wiley and Sons: New York, 1991; 17-245.
2. 3, and (3) NaOH in 76% yield.
3. Burton, D.J.; Koppes, W.M. Chem. Commun. 1973, 425.
4. Driguez, Z.; Henrissat, B. Tetrahedron Lett. 1981, 22, 5061-5062.
5. The structure of 12 was confirmed after converting into known acetate as described in experimental section.
6. During the reaction, only starting 7 and thiirane 5 were observed by TLC. No intermediate material was detected.
7. Yuasa, H.; Tamura, J.; Hashimoto, H. J. Chem. Perkin Trans. I 1990, 2763.
8. [2] also gave alcohol 12 in slightly lower yield (59%) along with unknown by-product.