Methyldopa → (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

HRID 127004

Reaktionsgleichung

Reaktionsgleichung von HRID 127004
[CH3:1][C@@:2]([NH2:15])([C:12]([OH:14])=[O:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([OH:11])[CH:5]=1.[CH3:16][C:17]([O:20][C:21](OC1C(Cl)=CC(Cl)=C(Cl)C=1)=[O:22])([CH3:19])[CH3:18]>CN(C)C=O>[C:17]([O:20][C:21]([NH:15][C@:2]([CH3:1])([C:12]([OH:14])=[O:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([OH:11])[CH:5]=1)=[O:22])([CH3:19])([CH3:18])[CH3:16]

Komponenten

4

Edukt 2

HCID 38853MethyldopaHCID 86887tert-Butyl 2,4,5-trichlorophenyl carbonate

Produkt 1

HCID 15719345(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acidAusbeute 127 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1.19 g (5.00 m moles) L-3-(3,4-dihydroxyphenyl)-2-methylalanine, 1.49 g (5.00 m moles) t-butyl 2,4,5-trichlorophenylcarbonate and 6 ml dimethylformamide is flushed with nitrogen and 1.39 ml (10.0 m moles) triethylamine is added. After stirring at room temperature for 24 hours, 60 ml H2O and 4 ml 2.5 N HCl is added. The solution is extracted 3 times with 50 ml of ethyl acetate and the extract is washed 3 times with 50 ml of water and 1 time with 50 ml of saturated sodium chloride solution and is dried (MgSO4). The solvent is removed in vacuum to give 1.98 g of a blue oil.

Aufarbeitung

  1. customis flushed with nitrogen and 1.39 ml (10.0 m moles) triethylamine
  2. additionis added
  3. addition60 ml H2O and 4 ml 2.5 N HCl is added
  4. extractionThe solution is extracted 3 times with 50 ml of ethyl acetate
  5. washthe extract is washed 3 times with 50 ml of water and 1 time with 50 ml of saturated sodium chloride solution
  6. dry with materialis dried (MgSO4)
  7. customThe solvent is removed in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-97f5d199c7424bcbb3055272cccea655
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254273

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