Reaktion #49695

Reaktionsgleichung

ester C

DCC

DMF

→

tert-butyl propanoate

Reaktionsbedingungen

Vorschrift

36-Cascade:methane[4]:(3-oxo-6-oxa-2-azaheptylidyne):(3-oxo-2-azapentylidyne):tert-butyl propanoate (16) was prepared (57%), as a spongy white solid, from dodecaacid 11 (5.63 g, 4.2 mmol), amine 2 (21.98 g, 52.9 mmol), DCC (10.89 g, 52.9 mmol) 1-HBT (7.14 g, 52.9 mmol), and DMF (250 mL) via Procedure A: 14.55 g; mp 67°-70° C.; 1H NMR δ1.42 (s, CH3, 324H), 1.95, 2.20 (m, CH2CH2CO, 192H), 2.37 (t, J=5.7Hz, OCH2CH2CO, 8H), 3.32 (s, CH2O, 8H), 3.66 (t, J=5.7 Hz, OCH2, 8H), 6.36 (s, NH, 16H); 13C NMR δ28.1 (CH3), 29.7 (CH2CH2CO), 37.4 (OCH2CH2CO), 45.4 (4°CCore), 57.3 (4°CNH), 67.7 (CH2O), 68.9 (OCH2), 80.4 (CMe3), 170.7 (CONH), 172.6 (CO2); IR 3311 (NH), 1730 (ester C=O), 1661 (amide C=O), 1157, (ester C--O) cm-1. Anal. Calcd for C321H556N16O92 : C, 63.08; H, 9.17; N, 3.67. Found: C, 63.18; H, 8.89; N. 3.79.

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