Reaktion #2446108

Reaktionsgleichung

Compound 1

3-(4-chlorophenyl)adamantane-1-carboxylic acid [2-(3,4-dihydroxyphenyl)ethyl]amide

→

Compound 3

propionic acid 2-propionyloxy-5-(2-{[3-(4-chlorophenyl)adamantane-1-carbonyl]amino}ethyl)phenyl ester

Lösungsmittel

propionic anhydride

H2SO4

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe solution was then concentrated under a vacuum
2. 2
   Filtrationfiltered

Vorschrift

Compound 1 was dissolved in propionic anhydride with a catalytic amount of 98% H2SO4 and stirred under N2 for 3 days at room temperature. The solution was then concentrated under a vacuum and filtered to give the product Compound 3, with a melting point of 114-115° C. 1H NMR (500 MHz, CDCl3) δ 1.24-1.30 (m, 6H, 2CH3), 1.74 (m, 2H, Admant-H), 1.84-1.87 (m, 8H, Admant-H), 1.93 (s, 2H, Admant-H), 2.26 (m, 2H, Admant-H), 2.53-2.61 (m, 4H, 2COCH2), 2.82-2.85 (t, J=7.5 Hz, 2H, CH2), 3.50-3.54 (q, 2H, NCH2), 5.40 (s, 1H, NH), 7.01-7.02 (d, J=5 Hz, 1H, Ar—H), 7.06-7.08 (d, d, 1H, H—Ar), 7.13-7.15 (d, J=10 Hz, 1H, Ar—H), 7.30 (s, 4H, Ar—H); 13C NMR (500 MHz, CDCl3) δ 9.1, 27.5, 28.8, 35.0, 35.5, 36.5, 38.3, 40.3, 41.7, 42.0, 44.5, 123.5, 123.9, 126.4, 126.8, 128.3, 131.5, 137.8, 140.7, 142.1, 148.4, 171.7, 171.8, 177.4; MS m/z (relative intensity) 538.61 (MH+, 100), 539.61 (38), 540.61 (45).

Quelle