Réaction #60634

Équation de réaction

EA

triethylamine

K2CO3

2-{[1-({[(3S)-1-(2-Ethoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-[isopropyl(methyl)amino]-4-oxobutanoic acid

→

title compound

1-[(Ethoxycarbonyl)oxy]ethyl 2-{[1-({[(3S)-1-(2-ethoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-[isopropyl(methyl)amino]-4-oxobutanoate

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Lavageconsecutively washed with an aqueous KHSO4 solution and with brine
2. 2
   SéchageDrying of the organic layer over magnesium sulfate and column chromatography on silica gel (liquid phase: EA/cyclohexane 1:1(v/v))

Mode opératoire

107 mg of 2-{[1-({[(3S)-1-(2-Ethoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-[isopropyl(methyl)amino]-4-oxobutanoic acid (for preparation see example 72) was dissolved in 1 ml of DMF. Then 83 μl of triethylamine, 20 mg of solid K2CO3 and 85 μl of chloroethylethylcarbonate was added. After stirring over night the mixture was diluted with EA and consecutively washed with an aqueous KHSO4 solution and with brine. Drying of the organic layer over magnesium sulfate and column chromatography on silica gel (liquid phase: EA/cyclohexane 1:1(v/v)) yielded 41 mg of the title compound as a white foam, MS: [M+H]+: 660; m/z: 526, 449, 310, 253.

Source