反応 #1994334

反応方程式

N-(tert-butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-[(2S)-2-amino-3-phenylpropyl]-D-alaninamide

N,N′-Bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine

N,N-diisopropylethylamine

→

title compound

収率 81.0%

N-(tert-butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-[(2S)-2-{[(E)-{[(benzyloxy) carbonyl]amino}{[(benzyloxy)carbonyl]imino}methyl]amino}-3-phenylpropyl]-D-alaninamide

収率 81.0%

溶媒

THF

反応条件

後処理

1. 1
   その他quenched by the addition of water (5 mL)
2. 2
   抽出The mixture was extracted with ethyl acetate (10 mL)
3. 3
   乾燥the extract was dried over sodium sulphate
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他The residue was purified by column chromatography (silica, 25% ethyl acetate in heptane as eluent increasing to 33%)

実験手順

To a solution N-(tert-butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-[(2S)-2-amino-3-phenylpropyl]-D-alaninamide (330 mg, 0.64 mmol) from preparation 33 in THF (5 mL) was added N,N′-Bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine (268 mg, 0.71 mmol) and N,N-diisopropylethylamine (173 uL, 0.97 mmol). The reaction was stirred for 2 hours at 60° C. and then quenched by the addition of water (5 mL). The mixture was extracted with ethyl acetate (10 mL), the extract was dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 25% ethyl acetate in heptane as eluent increasing to 33%) to afford the title compound as a colourless oil in 81% yield, 430 mg. 1H NMR (400 MHz, MeOH-d4) δ : 1.05 (d, 3H), 1.28 (s, 9H), 2.22 (s, 6H), 2.73-3.11 (m, 4H), 3.41-3.52 (m, 1H), 3.95-4.23 (m, 2H), 4.38-4.59 (m, 2H), 4.98-5.28 (m, 4H), 6.45 (s, 2H), 7.09-7.46 (m, 15H). LRMS APCI m/z 823 [MH]+

出典