Bromotrimethylsilane → (14R,18R)-14-amino-18-(dodecyloxy)-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontylphosphonic acid

HRID 2407920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407920
[NH2:1][C@@H:2]([CH2:25][S:26][CH2:27][C@H:28]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:3](=[O:24])[NH:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][P:16](=[O:23])([O:20]CC)[O:17]CC.C[Si](Br)(C)C>C(Cl)Cl>[NH2:1][C@@H:2]([CH2:25][S:26][CH2:27][C@H:28]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:3](=[O:24])[NH:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][P:16](=[O:17])([OH:23])[OH:20]

Komponenten

4

Edukt 2

HCID 76113BromotrimethylsilaneHCID 86678305diethyl (14R,18R)-14-amino-18-(dodecyloxy)-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontylphosphonate

Produkt 1

HCID 53476548(14R,18R)-14-amino-18-(dodecyloxy)-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontylphosphonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of diethyl (14R,18R)-14-amino-18-(dodecyloxy)-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontylphosphonate (1 eq) in DCM (0.1 M) was added trimethylsilyl bromide (20 eq). The reaction mixture was stirred at room temperature overnight and then concentrated. The crude mixture was purified by reverse phase high performance liquid chromatography (HPLC) with C4 column eluting with a gradient of 50-100% MeCN/10 mM NH4OAc (95:5) in 10 mM NH4OAc (pH 9) to give the title compound as a white solid. 1H NMR (CDCl3): δ 8.73 (br s, 1H), 4.17 (br s, 1H), 3.70-3.83 (m, 3H), 3.57-3.70 (m, 10H), 3.50-3.57 (m, 4H), 3.45-3.50 (m, 2H), 3.33-3.45 (m, 4H), 3.02-3.16 (m, 2H), 2.65-2.79 (m, 2H), 1.90 (dd, 2H), 1.47-1.61 (m, 4H), 1.16-1.36 (m, 36H), 0.88 (t, 6H). LRMS [M+H]=771.5.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe crude mixture was purified by reverse phase high performance liquid chromatography (HPLC) with C4 column
  3. washeluting with a gradient of 50-100% MeCN/10 mM NH4OAc (95:5) in 10 mM NH4OAc (pH 9)

Quellen und Nachweise

ORD-Eintrag
ord-5bf46abbf3e546a1a5a0034a556ace5d
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08808703B2

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