Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1985-06-19
1987-03-24
Daus, Donald G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
560174, C07D27740, C07D27742, C07D27744, C07D27748
Patent
active
046526528
ABSTRACT:
A useful intermediate for synthesizing penicillins or cephalosporins {i.e., 1-(2-protected amino-4-thiazolyl)propene-1,3-dicarboxylic acid half ester (VI)} is prepared by a process comprising (1) treating haloacetylmalonic acid ester (I) with thiourea to give 2-(2-amino-4-thiazolyl)malonic acid ester (II), (2) protecting the amino group of the latter to give 2-(2-protected amino-4-thiazolyl)malonic acid ester (III), (3) treating the product with haloalkenoic acid ester to give 1-(2-protected amino-4-thiazolyl)-2-propene-(1,1,3-tri or 1,1,3,3-tetra)carboxylic acid ester (IV), (4) hydrolyzing and decarboxylating the latter to give 1-(2-protected amino-4-thiazolyl)propene-1,3-dicarboxylic acid (V), and (5) treating the product with alcohol and a hemi-esterifying reagent to give the objective 1-(2-protected amino-4-thiazolyl)propene-1,3-dicarboxylic acid half ester (VI).
REFERENCES:
patent: 4298375 (1981-11-01), Howe et al.
Hamashima, Chemical Abstracts, vol. 103:104789a, (1985).
Matsumura Hiromu
Yano Toshisada
Daus Donald G.
Kapner Stephen M.
Shionogi & Co. Ltd.
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