Triethylamine → N-(1-adamantylcarbonyl)-L-alanyl-L-proline ethylamide

2.93 g (0.010 mol) of L-alanyl-L-proline ethylamide hydrobromide were dissolved in 50 ml of tetrahydrofuran and the mixture was cooled to 0° C. There were then added 2.8 ml (0.020 mol) of triethylamine followed by 2.15 g (0.010 mol) of 1-adamantoyl chloride. The mixture was stirred at 0° C. for 0.5 hour and at room temperature for 2 hours and then evaporated to dryness. The oily residue was dissolved in ethyl acetate and the solution washed successively with 0.5-N hydrochloric acid, water, 5% sodium bicarbonate solution and water, dried over sodium sulphate and evaporated. The resulting oil was crystallised from ethyl acetate/petroleum ether to yield 2.2 g (59%) of N-(1-adamantylcarbonyl)-L-alanyl-L-proline ethylamide of melting point 116°-118° C; [α]D20 =-88.1° (c=0.99% in methanol).

1. customevaporated to dryness
2. dissolutionThe oily residue was dissolved in ethyl acetate
3. washthe solution washed successively with 0.5-N hydrochloric acid, water, 5% sodium bicarbonate solution and water
4. dry with materialdried over sodium sulphate
5. customevaporated
6. customThe resulting oil was crystallised from ethyl acetate/petroleum ether

ORD record

ord-e94567f951974e3e91e1002d8f91b1cb

Source dataset

uspto-grants-1979_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04176116