Nalpha-(9-fluorenylmethoxycarbonyl)-Nepsilon-(4,4-bis(diallylphosphoryl)butyryl)-L-lysine → Nepsilon-(4,4-bis(diallylphosphoryl)butyryl)-L-lysine

HRID 39270

Reaktionsgleichung

Reaktionsgleichung von HRID 39270
C1C2C(COC([NH:18][C@H:19]([C:46]([OH:48])=[O:47])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:45])[CH2:26][CH2:27][CH:28]([P:37]([CH2:42][CH:43]=[CH2:44])([CH2:39][CH:40]=[CH2:41])=[O:38])[P:29]([CH2:34][CH:35]=[CH2:36])([CH2:31][CH:32]=[CH2:33])=[O:30])=O)C3C(=CC=CC=3)C=2C=CC=1>N1CCCCC1.CN(C=O)C.C(OCC)(=O)C>[CH2:31]([P:29]([CH:28]([P:37]([CH2:39][CH:40]=[CH2:41])([CH2:42][CH:43]=[CH2:44])=[O:38])[CH2:27][CH2:26][C:25]([NH:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]([C:46]([OH:48])=[O:47])[NH2:18])=[O:45])([CH2:34][CH:35]=[CH2:36])=[O:30])[CH:32]=[CH2:33]

Komponenten

4

Edukt 1

HCID 86762028Nalpha-(9-fluorenylmethoxycarbonyl)-Nepsilon-(4,4-bis(diallylphosphoryl)butyryl)-L-lysine

Produkt 1

HCID 86762027Nepsilon-(4,4-bis(diallylphosphoryl)butyryl)-L-lysineAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 23501187piperidine N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. washwas washed with water and brine
  2. dry with materialthen dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by silica gel chromatography (methanol in ethyl acetate, 5% over 5 column volumes

Quellen und Nachweise

ORD-Eintrag
ord-9ace8feb681144c797b9b24e1829a87f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524691B2

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