Reacción #417908

Ecuación de reacción

N-(6-hydroxyhexyl)prop-2-enyloxycarboxamide

Et3N

NH4Cl

MsCl

→

6-(Prop-2-enyloxycarbonylamino)hexyl methylsulfonate

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting solution was warmed to 22° C.
2. 2
   Otrotransferred to a separatory funnel
3. 3
   OtroThe layers separated
4. 4
   Lavadothe aqueous layer washed with CH2Cl2 (3×50 mL)
5. 5
   LavadoThe combined washes were washed with 20% aqueous NaCl
6. 6
   Secadothen dried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo to a pale yellow oil (3.2 g) that
9. 9
   Otrowas used without further purification in the subsequent alkylation step

Procedimiento

A solution of N-(6-hydroxyhexyl)prop-2-enyloxycarboxamide (2.55 g, 12.7 mmol; Charreyre, M. T.; Boullanger, P.; Pichot, C.; Delair, T.; Mandrand, B.; Llauro, M. F. Mak. Chem. 1993, 194(1), 117-35.) in dry CH2Cl2 (30.0 mL) was treated with Et3N (4.06 mL, 29.1 mmol) then cooled to 0° C. To this solution was transferred MsCl (15.2 mmol; 20.0 mL of a 0.76 M solution in CH2Cl2) using a cannula; full conversion coincided with completion of the transfer. The resulting solution was warmed to 22° C., then treated with 2 M NH4Cl (50 mL) and transferred to a separatory funnel. The layers separated and the aqueous layer washed with CH2Cl2 (3×50 mL). The combined washes were washed with 20% aqueous NaCl then dried over MgSO4, filtered and concentrated in vacuo to a pale yellow oil (3.2 g) that was used without further purification in the subsequent alkylation step. 1H NMR (CDCl3, 300 MHz): δ 5.90 (1H, ddt, J=17.2, 10.4, 5.6 Hz), 5.29 (1H, dq, J=17.2, 1.6 Hz), 5.19 (1H, dq, J=10.4, 1.3 Hz), 4.71 (1H, brs), 4.54 (2H, brd, J=5.5 Hz), 4.20 (2H, t, J=6.5 Hz), 3.17 (2H, brs), 2.98 (3H, s), 1.79-1.69 (2H, m), 1.55-1.29 (6H, m).

Fuente