Reaktion #598841

Reaktionsgleichung

3-{3-[{[(3aR,4R,6R,6aS)-6-{6-[(2,4-dimethoxybenzyl)amino]-9H-purin-9-yl}-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl}{isopropyl)amino]cyclobutyl}propanoic acid

N,N-Diisopropylethylamine

4-tert-butylbenzene-1,2-diamine

NaHCO3

→

amide

Ausbeute 91.9%

N-(2-amino-4-(tert-butyl)phenyl)-3-(3-((((1R,2R,3S,4R)-4-(6-((2,4-dimethoxybenzyl)amino)-9H-purin-9-yl)-2,3-dihydroxycyclopentyl)methyl)(isopropyl)amino)cyclobutyl)propanamide

Ausbeute 91.9%

Lösungsmittel

N,N-Dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture extracted with EtOAc (3×)
2. 2
   Trocknenthe combined organics was dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified by flash chromatography (DCM→DCM/7N NH3 in MeOH 95:5)

Vorschrift

N,N,N′,N′-Tetramethyl-0-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (1.19 g, 3.13 mmol) added to a solution of 3-{3-[{[(3aR,4R,6R,6aS)-6-{6-[(2,4-dimethoxybenzyl)amino]-9H-purin-9-yl}-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl}{isopropyl)amino]cyclobutyl}propanoic acid (1.30 g, 2.09 mmol) and N,N-Diisopropylethylamine (1.20 ml, 6.89 mmol) and 4-tert-butylbenzene-1,2-diamine (0.411 g, 2.50 mmol) in N,N-Dimethylformamide (12.9 ml). The reaction was stirred for 2 hours, NaHCO3 (saturated) was added and the mixture extracted with EtOAc (3×) and the combined organics was dried over MgSO4 filtered and concentrated. The residue was purified by flash chromatography (DCM→DCM/7N NH3 in MeOH 95:5) to yield the desired amide (1.4 g) as a solid.

Quelle