Pyridine → N-methoxycarbonyl-L-tyrosine benzyl ester

HRID 274087

Reaktionsgleichung

Reaktionsgleichung von HRID 274087
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:31])[C@H:21]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1.ClCCl.Cl[C:42]([O:44][CH3:45])=[O:43]>O>[CH2:12]([O:19][C:20](=[O:31])[C@H:21]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=1)[NH:22][C:42]([O:44][CH3:45])=[O:43])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 104540O-benzyl-L-tyrosine toluene-p-sulphonate

Produkt 1

HCID 54118506N-methoxycarbonyl-L-tyrosine benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To an ice-cooled mixture of L-tyrosine benzyl ester p-toluenesulfonate (41.0 g), pyridine (16.4 ml), and dichloromethane (92 ml) was added methyl chloroformate (7.8 ml). The mixture was stirred in an ice-bath for 1 hour, diluted with water, and extracted once with dichloromethane. The extract was concentrated in vacuo and the residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Purification of the crude product by column chromatography on silica gel (gradient elution; 10:1 to 5:1 chloroform-ethyl acetate) gave N-methoxycarbonyl-L-tyrosine benzyl ester (22.0 g).

Aufarbeitung

  1. extractionextracted once with dichloromethane
  2. concentrationThe extract was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude product by column chromatography on silica gel (gradient elution; 10:1 to 5:1 chloroform-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a8b25bcf9a0b44ff970acb08cc2a1871
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387710

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