Reacción #940057

Ecuación de reacción

( 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

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux for 48 h
3. 3
   OtroThe organic phase was decanted
4. 4
   Lavadothe remaining gum washed several times with CH2Cl2
5. 5
   FiltraciónThe washings were filtered (Celite™)
6. 6
   OtroEvaporation of the solvent under reduced pressure

Procedimiento

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)+.

Fuente