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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 (2000)

Apparu, Marcel ; Tiba, Younes Ben ; Léo, Pierre-Marc ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 1007-1012

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ISSN: 1434-193X

Keywords: β-Blockers ; Protecting groups ; Deprotection ; Carbamates ; Oxazolidinone ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---The iodinatied carbamates 3 (E + Z), with potential β-blocking properties, were synthesized. The first route chosen, from 4-aminophenol and the chloroformate β7, 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).

Type of Medium: Electronic Resource

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