반응 #67548

반응 방정식

90

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

→

liquid 91

수율 85.6%

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

수율 85.6%

용매

piperidine DMF

ethyl acetate

반응 조건

후처리

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

실험 절차

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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