Reaktion #67548

Reaktionsgleichung

90

Nα-(9-fluorenylmethoxycarbonyl)-Nε-(4,4-bis(diallylphosphoryl)butyryl)-L-lysine

→

liquid 91

Ausbeute 85.6%

Nε-(4,4-bis(diallylphosphoryl)butyryl)-L-lysine

Ausbeute 85.6%

Lösungsmittel

piperidine DMF

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwas washed with water and brine
2. 2
   Trocknenthen dried over Na2SO4
3. 3
   Einengenconcentrated in vacuo
4. 4
   SonstigeThe crude material was purified by silica gel chromatography (methanol in ethyl acetate, 5% over 5 column volumes

Vorschrift

A solution of 90 (502 mg, 0.616 mmol) in piperidine/DMF (0.05:1, 5 mL) was stirred at room temperature for 18 hr. After diluting with ethyl acetate (40 mL) the organic layer was washed with water and brine then dried over Na2SO4 and concentrated in vacuo. The crude material was purified by silica gel chromatography (methanol in ethyl acetate, 5% over 5 column volumes then 5 to 30% over 10 column volumes) using a Biotage Horizon™ apparatus resulting in the colourless liquid 91 (249 mg, 68%): 1H NMR (400 MHz, CDCl3) δ 1.39-1.74 (m, 6H), 1.45 (s, 9H), 2.21-2.35 (m, 2H), 2.51 (t, J=7.4, 2H), 2.55 (tt, J=6.9, 23.9, 1H), 3.19-3.25 (m, 2H), 3.29 (dd, J=5.2, 7.6, 1H), 4.58-4.63 (m, 8H), 5.25 (dq, J=1.3, 10.3, 4H), 5.38 (dq, J=1.4, 17.1, 4H), 5.90-6.00 (m, 4H), 6.14 (bd, J=4.9, 1H): 31P (162 MHz, CDCl3) δ 24.67 (s, 2P).

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