Water → N-benzyloxycarbonyl-l-tyrosine

HRID 1590614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590614
[OH2:1].[H-].[Na+].[C:4]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br)([O:6][C:7]([CH3:10])(C)C)=[O:5]>CCOC(C)=O.C(Cl)Cl>[C:4]([NH:11][C@H:12]([C:4]([OH:6])=[O:5])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([OH:1])=[CH:18][CH:19]=1)([O:6][CH2:7][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24758Sodium hydrideHCID 103578931,1-Dimethylethyl N-(8-bromooctyl)carbamate

Produkt 1

HCID 712438N-benzyloxycarbonyl-l-tyrosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226138Dichloromethane ethylacetateLösungsmittel

Versuchsvorschrift

H2O (1.5 g, 4.29 mmole) was dissolved in EtOAc/CH2Cl2, dried over MgSO4, filtered and evaporated. The residue was dissolved in DMF and treated with NaH (50% dispersion in oil, 0.43 g, 8.96 mmole) for 1 hour. N-BOC-8-amino-1-bromooctane (1.33 g, 4.34 mmole) was added and the reaction was stirred for 16 hours. The DMF was removed in vacuo, the residue dissolved in water, acidified to pH 3 and extracted with EtOAc. The EtOAc layers were combined, dried and concentrated. Column chromatography (SiO2, 97:3:1 CHCl3 /MeOH/HOAc) gave 2-5.

Aufarbeitung

  1. dry with materialdried over MgSO4
  2. filtrationfiltered
  3. customevaporated
  4. dissolutionThe residue was dissolved in DMF
  5. customThe DMF was removed in vacuo
  6. dissolutionthe residue dissolved in water
  7. extractionextracted with EtOAc
  8. customdried
  9. concentrationconcentrated
  10. customColumn chromatography (SiO2, 97:3:1 CHCl3 /MeOH/HOAc) gave 2-5

Quellen und Nachweise

ORD-Eintrag
ord-5f7867d2968c48bd8e905017c97e2086
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204350

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