Potassium Phosphate, Tribasic → HCID 18631278, Verbindung

HRID 1195001Notizen

Reaktionsgleichung

FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[C:16]12([CH2:26][CH2:27]O)[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.C(N(C(C)C)CC)(C)C.[CH3:38][O:39][C:40](=[O:63])[C@H:41]([CH2:50][C:51]1[N:55]=[CH:54][N:53](C(OC(C)(C)C)=O)[CH:52]=1)[NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl>[CH3:38][O:39][C:40](=[O:63])[C@H:41]([CH2:50][C:51]1[N:55]([CH2:27][CH2:26][C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[CH2:17]2)[CH2:23]3)[CH:54]=[N:53][CH:52]=1)[NH:42][C:43]([O:45][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:44]

Komponenten

Reaktionsbedingungen

Temperatur: -55 °C

Versuchsvorschrift

A solution of 11.8 mL trifluoromethanesulfonic anhydride in 70 mL dichloromethane is chilled to -70° C. and treated dropwise with a solution composed of 12.6 g 1-adamantyl-2-hydroxyethane, 12.2 mL diisopropylethylamine and 70 mL dichloromethane. The solution is allowed to warm to -55° C. over 45 min then a solution of 25 g N,1-bis-BOC-histidine methyl ester (J. Chem. Soc., Perkin Trans. I 1982; 1553-61.) in 70 mL dichloromethane is added dropwise. The reaction is then stirred at 25° C. for 24 hr and poured into pH=7, 0.25M potassium phosphate buffer (500 mL), stirring vigorously. The organic layer is separated, washed with the same buffer, dried and concentrated. 3-(2-(1-Adamantyl)ethyl)-N-BOC-histidine methyl ester is isolated by chromatography on silica gel (chloroform-methanol, 99:1) as a gum. NMR (CDCl3) 3.85 (m, 2H, NCH2).

Aufarbeitung

additiontreated dropwise with a solution
stirringstirring vigorously
customThe organic layer is separated
washwashed with the same buffer,
customdried
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-c882b85770e9485eb1def7c4898e5720
Quelldatensatz: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04816463

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