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Paper | Regular issue | Vol 27, No. 12, 1988, pp.2815-2823
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4651
Preparation of D-Penicillamine. Reaction of Penilloic Acid, Penicilloic Acid α-Amides and Benzylpenicillin with N,N‘-Diphenylethylenediamine

Toshihisa Ogawa,* Kazuyuki Tomisawa, and Kaoru Sota

*Research Center, Taisho Pharmaceutical Co., Ltd., 1-403 Yoshino-Cho, Saitama-city, Saitama 330-8530, Japan

Abstract

Reaction of benzylpenilloic acid (1) with N,N’-diphenylethylenediamine (2) in mixture of water, acetic acid and toluene under reflux yielded D-penicillamine (4). In a similar way, 4 was also obtained from benzyl- and phenoxymethylpenicilloic acid α-amides (6a-f) and benzylpenicillin potassium salt (13). The structures of the byproducts formed in these reactions were also determined.