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

HRID 2205023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2205023
[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-0e625fd019074c7782f98f26eda85875
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365506B2

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