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Synthesis of Potentially β‐Blocking Practolol Derivatives: ( E + Z )‐3‐[4‐(3‐Iodoprop‐2‐enyloxycarbonylamino)phenoxy]‐1‐(isopropylamino)propan‐2‐ol
Author(s) -
Apparu Marcel,
Tiba Younes Ben,
Léo PierreMarc,
Fagret Daniel
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200003)2000:6<1007::aid-ejoc1007>3.0.co;2-i
Subject(s) - chemistry , practolol , chloroformate , carbamate , amine gas treating , blocking (statistics) , combinatorial chemistry , condensation , organic chemistry , medicinal chemistry , medicine , propranolol , statistics , physics , mathematics , thermodynamics
The iodinatied carbamates 3 ( E + Z), with potential β‐blocking properties, were synthesized. The first route chosen, from 4‐aminophenol and the chloroformate β 7 , had to be abandoned because of the formation of the oxazolidinone 10 during the epoxidation step. The aminoalcohol 17 prepared from the practolol 1 finally gave the target compounds by condensation with the iodoallylic chloroformates 8 ( E + Z ). The secondary Boc‐protected amine function was regenerated without removing the carbamate function situated in the p ‐postion, by using mild reaction conditions (1 N HCl).