Potassium Phosphate, Tribasic → 3-(2-methoxyphenyl)methyl-N-BOC-histidine methyl ester

HRID 1194150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1194150
CS(OS(C)(=O)=O)(=O)=O.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]O.C(N(C(C)C)CC)(C)C.[CH3:29][O:30][C:31](=[O:54])[C@H:32]([CH2:41][C:42]1[N:46]=[CH:45][N:44](C(OC(C)(C)C)=O)[CH:43]=1)[NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl>[CH3:29][O:30][C:31](=[O:54])[C@H:32]([CH2:41][C:42]1[N:46]([CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[O:11][CH3:10])[CH:45]=[N:44][CH:43]=1)[NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:35]

Komponenten

7

Edukt 5

HCID 62657Potassium Phosphate, TribasicHCID 691542-Methoxybenzyl alcoholHCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 10904703N(alpha), N-(im)-Di-Boc-L-histidine methyl ester

Produkt 1

HCID 186312793-(2-methoxyphenyl)methyl-N-BOC-histidine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 8 g methanesulfonic anhydride in 45 mL dichloromethane is chilled to -50° C. and treated dropwise with a solution of 6.2 mL 2-methoxybenzyl alcohol, 8.0 mL diisopropylethylamine and 45 mL dichloromethane. The resulting solution is warmed to 0° C. over 30 min and treated dropwise with 15.0 g N,1-bis-BOC-histidine methyl ester dissolved in 45 mL dichloromethane. The mixture is then heated at reflux 24 hr, poured into 400 mL 0.25M, pH=7 potassium phosphate buffer and the organic layer is separated, dried and evaporated. Chromatography on silica gel, eluting with chloroform-methanol (99:1) gives 3-(2-methoxyphenyl)methyl-N-BOC-histidine methyl ester as a gum. NMR (CDCl3) 4.96 (s,2H,NCH2Ar).

Aufarbeitung

  1. temperatureThe mixture is then heated
  2. temperatureat reflux 24 hr
  3. customthe organic layer is separated
  4. customdried
  5. customevaporated
  6. washChromatography on silica gel, eluting with chloroform-methanol (99:1)

Quellen und Nachweise

ORD-Eintrag
ord-90d12253e8ce4164badf3b1a59f4fb2b
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04812462

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