Reaktion #598856

Reaktionsgleichung

benzyl 3-[3-({[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl}(propan-2-yl)amino)cyclobutyl]propanoate

→

3-[3-({[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl}(propan-2-yl)amino)cyclobutyl]propanoic acid

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was continued stirring under hydrogen for 4 hours
2. 2
   FiltrationThis was filtered
3. 3
   Sonstigeevaporated in vacuo
4. 4
   Sonstigeevaporated from DCM (2×20 ml)
5. 5
   Sonstigeto give 680 mg (quant.) of a white foamy solid
6. 6
   SonstigeHPLC purity 100% (ret. time, 1.11 min)

Vorschrift

10% Pd—C (70 mg) was added to a solution of benzyl 3-[3-({[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl}(propan-2-yl)amino)cyclobutyl]propanoate (790 mg, 1.40 mmol) in EtOH (20 ml) and stirred under an atmosphere of hydrogen for 18 hours at RT. A further aliquot of 10% Pd—C (70 mg) was added and the reaction was continued stirring under hydrogen for 4 hours. This was filtered and evaporated in vacuo, and then evaporated from DCM (2×20 ml) to give 680 mg (quant.) of a white foamy solid; MS (ESI+) for C23H34N6O5 m/z 475.20 [M+H]+; HPLC purity 100% (ret. time, 1.11 min); 1H NMR (500 MHz, CHLOROFORM-d) δH ppm 8.29 (d, J=16.3 Hz, 1H), 7.97 (d, J=16.2 Hz, 1H), 6.86 (s, 2H), 6.05 (dd, J=4.3, 1.7 Hz, 1H), 5.66-5.43 (m, 1H), 5.00 (ddd, J=19.3, 6.3, 3.2 Hz, 1H), 4.30 (s, 1H), 3.47-2.85 (m, 2H), 2.60 (ddd, J=38.8, 24.1, 13.5 Hz, 2H), 2.19 (ddd, J=14.7, 11.9, 7.1 Hz, 2H), 2.07-1.94 (m, 2H), 1.81 (dd, J=65.1, 6.9 Hz, 3H), 1.66-1.46 (m, 5H), 1.45-1.22 (m, 4H), 1.00 (d, J=6.4 Hz, 3H), 0.89 (dd, J=12.2, 6.6 Hz, 3H).

Quelle