Reaction #2446109

Reaction equation

Compound 1

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

→

Compound 4

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

Solvents

n-butyric anhydride

H2SO4

Conditions

Workup

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

Procedure

Compound 1 was dissolved in n-butyric 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 4, with a melting point of 78-80° C. 1H NMR (500 MHz, CDCl3) δ 1.03-1.08 (m, 6H, 2CH3), 1.74 (m, 2H, Admant-H), 1.75-1.87 (m, 12H, 2CH2, Admant-H), 1.93 (s, 2H, Admant-H), 2.26 (m, 2H, Admant-H), 2.49-2.55 (m, 4H, 2COCH2), 2.82-2.85 (t, J=7.5 Hz, 2H, CH2), 3.50-3.54 (q, 2H, NCH2), 5.69 (s, 1H, NH), 7.01-7.02 (d, J=5 Hz, 1H, Ar—H), 7.06-7.08 (d, d, 1H, H—Ar), 7.12-7.14 (d, J=10 Hz, 1H, Ar—H), 7.30 (s, 4H, Ar—H); MS m/z (relative intensity) 566.73 (MH+, 50), 567.61 (12), 568.60 (20).

Source