Hydrogen Bromide → HCID 20446777, compound

Participants

Reaction Steps

A solution of 1-(3,4-dihydroxyphenyl)-2-[1,1-dimethyl-2-(2-phenoxyacetamido)ethylamino]ethanol hydrobromide (0.8 g.) in trifluoroacetic acid (5.4 ml.) was treated with pivaloyl chloride (1.12 ml.) and the mixture was heated under reflux for 40 minutes. The mixture was then evaporated and the residue was dissolved in ether. The solution obtained was treated with ethereal hydrogen bromide until just acid, where upon an oily solid separated. Trituration of this material with ether (20 ml.) gave the triester, 1-[3,4-bis(pivaloyloxy)phenyl]-2-[1,1-dimethyl-2-(2-phenoxyacetamido)ethylamino]ethyl pivaloate hydrobromide, as a solid (0.6 g.) m.p. 106°-110° C., NMR δ: 8.8 (2H, broad singlet, N+H2); 8.45 (1H, triplet, NHCO); 7.8-6.8 (8H, complex, aromatic protons); 5.43 (1H, broad, =CHO); 3.58 (2H, singlet, CHHD 2OPh); 4.0-3.0 (complex, CH2NH); 1.3-1.2 (33H, broad singlet, C.CH3).

Provenance & Evidence