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US 4,275,207 AGranted
Process for preparing 7-(1-hydroxyethyl)-3-(2-aminoethylthio)-1-carbadethiaceph-3-em-3-carboxy lic acid and intermediate therefor
AssigneeMerck & Co., Inc.
InventorsRonald W. Ratcliffe, Thomas N. Salzmann
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Abstract
Disclosed is a process for preparing 7-(1-hydroxethyl)-3-(2-aminoethylthio)-1-carbadethiaceph-3-em-3-carboxylic acid and its pharmaceutically acceptable salts and esters (I) by total synthesis starting with L-aspartic acid and proceeding via intermediate II: ##STR1## R=blocking group
Claims3
A process for preparing a compound having the structure:
- which comprises the steps of cyclizing:
- ##STR24## in the presence of a catalyst selected from:
- bis(acetylacetonato)Cu, ##STR25## to form:
- ##STR26## followed by esterifying to form:
- ##STR27## followed by alkylating in the presence of base with acetaldehyde to form:
- ##STR28## followed by treating with aminoethylmercaptan and deblocking wherein R is a readily removable carboxyl blocking group selected from the group consisting of t-butyl, p-methoxybenzyl, benzhydryl, p-nitrobenzyl, and p-methoxybenzyl and R.degree. is a leaving group selected from the group consisting of tosyl, mesyl, or nosyl.
3 more elements
A compound having the structure:
- ##STR29## wherein R is a blocking group selected from the group consisting of t-butyl, p-methoxybenzyl, benzhydryl, p-nitrobenzyl, and p-nitrobenzyl.
A process for preparing a compound having the structure:
- ##STR30## which comprises cyclizing:
- ##STR31## in the presence of a catalyst selected from:
- bis(acetylacetonato)Cu, ##STR32## wherein R is a readily removable carboxyl blocking group selected from the group consisting of t-butyl, p-methoxybenzyl, benzhydryl, p-nitrobenzyl, and p-nitrobenzyl.
Dependencies are inferred from the claim text.