Reaktion #940057

Reaktionsgleichung

( 65 )

(S)-7-Phenyl-heptanoic acid [1-(4-benzyloxy-benzyl)-3-cyano-propyl]-amide

NaN3

Et2NH.HCl

→

gum

(S)-7-Phenyl-heptanoic acid [1-(4-benzyloxy-benzyl)-3-(1H-tetrazol-5-yl)-propyl]-amide

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 48 h
3. 3
   SonstigeThe organic phase was decanted
4. 4
   Waschenthe remaining gum washed several times with CH2Cl2
5. 5
   FiltrationThe washings were filtered (Celite™)
6. 6
   SonstigeEvaporation of the solvent under reduced pressure

Vorschrift

A mixture of (65) (74 mg, 0.16 mmol), NaN3 (103 mg, 1.58 mmol) and Et2NH.HCl (173 mg, 1.58 mmol) in toluene (1.5 mL) was heated at reflux for 48 h. The organic phase was decanted, and the remaining gum washed several times with CH2Cl2. The washings were filtered (Celite™), and the organic phases combined. Evaporation of the solvent under reduced pressure afforded a brown gum (180 mg) which was chromatographed on a C-18 reverse phase column to provide (66) (29 mg, 36%). 1H NMR (500 MHz, d4-MeOH) δ 7.43-7.07 (m, 12H), 6.9 (d, 2H, J=8.6 Hz), 4.99 (s, 2H), 4.15-4.04 (m, 1H), 3.03-2.86 (m, 2H), 2.79 (dd, 1H, J=5.7, 13 Hz), 2.65 (dd, 1H, J=8.7, 13 Hz), 2.54 (t, 2H, J=7.6 Hz), 2.12-2.00 (m, 3H), 1.90-1.78 (m, 1H), 1.50-1.36 (m, 2H), 1.33-1.10 (m, 4H). 13C NMR (125 MHz, d4-MeOH) δ 176.2, 158.9, 156.2, 143.9, 138.8, 131.9, 131.3, 129.5, 129.4, 129.3, 128.8, 128.5, 126.6, 115.8, 71.0, 51.5, 41.1, 37.2, 36.8, 33.5, 32.5, 30.0 (two superimposed), 27.0, 21.3. ESMS 512 (M+H)+.

Quelle