Potassium Phosphate, Tribasic → 3-(3-methyl-4-methoxyphenyl)methyl-N-BOC-histidine methyl ester

HRID 1195008

Reaktionsgleichung

CS(OS(C)(=O)=O)(=O)=O.[CH3:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH2:14]O.C(N(C(C)C)CC)(C)C.[CH3:30][O:31][C:32](=[O:55])[C@H:33]([CH2:42][C:43]1[N:47]=[CH:46][N:45](C(OC(C)(C)C)=O)[CH:44]=1)[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl>[CH3:30][O:31][C:32](=[O:55])[C@H:33]([CH2:42][C:43]1[N:47]([CH2:14][C:13]2[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:11]([CH3:10])[CH:12]=2)[CH:46]=[N:45][CH:44]=1)[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36]

Komponenten

Reaktionsbedingungen

Temperatur: -25 °C

Versuchsvorschrift

A solution of 10.8 g methanesulfonic anhydride in 120 mL dichloromethane is chilled to -50° C. and treated dropwise with a solution of 9.4 g 3-methyl-4-methoxybenzyl alcohol, 10.8 mL diisopropylethylamine and 80 mL dichloromethane. The resulting solution is warmed to -25° C. over 30 min and treated dropwise with 20.0 g N,1-bis-BOC-histidine methyl ester dissolved in 125 mL dichloromethane. The mixture is then allowed to warm to 25° C. over 4 hr, stirring at this temperature 24 hr. The reaction mixture is poured into 700 mL 0.25M, pH=7 potassium phosphate buffer and the organic layer is separated, dried and evaporated. Chromatography on silica gel, eluting with chloroformmethanol (99:1) gives 3-(3-methyl-4-methoxyphenyl)methyl-N-BOC-histidine methyl ester as a gum. NMR (CDCl3) 1.43 (s, 9H, t-Bu).

Aufarbeitung

temperatureto warm to 25° C. over 4 hr
customthe organic layer is separated
customdried
customevaporated
washChromatography on silica gel, eluting with chloroformmethanol (99:1)

Quellen und Nachweise

ORD-Eintrag: ord-58156ff909384e0fb06d4ca807920cfb
Quelldatensatz: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04816463

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