Water → N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

HRID 980524

Reaktionsgleichung

Reaktionsgleichung von HRID 980524
[C:1]([NH:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:18](N(CC)CC)C.COS(OC)(=O)=O.O>CN(C)C=O>[CH3:18][O:16][C:15](=[O:17])[C@H:12]([CH2:13][OH:14])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 100310N-(Benzyloxycarbonyl)-L-serine

Produkt 1

HCID 6999535N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-CBZ-L-serine (25 g) was dissolved in 100 ml of dry N, N-dimethylformamide at 0° C. under argon. Triethylamine (2 e.g., 30 ml) and dimethylsulfate (20 ml) were added. The contents of the vessel were stirred overnight at room temperature and then poured into 500 ml of water and extracted with ethyl acetate (3×200 ml). The organic layer was washed with water and brine and dried with sodium sulfate. Rotary evaporation afforded an oil which crystallized after silica gel chromatography in pure ethyl ether. The structure of the product, N-CBZ-L-serine methyl ester, was confirmed by NMR spectroscopy.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×200 ml)
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried with sodium sulfate
  4. customRotary evaporation
  5. customafforded an oil which
  6. customcrystallized after silica gel chromatography in pure ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1553a016876f4d24bed21628b5337efa
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04638071

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