95519-32-7Relevant articles and documents
Diborane Reduction of Penicillins: Preparation of 7-Deoxopenicillanic Acid
Sammes, Peter G.,Smith, Steven,Woolley, Geoffrey T.
, p. 2603 - 2610 (2007/10/02)
The reduction of 6β-acylamidopenicillanates with diborane is shown to proceed by opening of the β-lactam ring to produce the corresponding amino alcohols.The chemistry of the reduction product from benzhydryl 6β-benzyloxycarbonylaminopenicillanate has been explored, in paticular its reaction with methanolic potassium hydroxide; no azetidines are formed.Cyclisation of the amino alcohol prepared from methyl penicillanate may be effected either indirectly, via the corresponding bromide, or directly, by use of a modified Mitsunobu reaction, to produce methyl 7-deoxypenicillanate.