2,6-Dichlorobenzoyl chloride → n-(2,6-Dichlorobenzoyl)-d-tyrosine methyl ester

HRID 24629

Reaktionsgleichung

Reaktionsgleichung von HRID 24629
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4](Cl)=[O:5].Cl.[CH3:13][O:14][C:15](=[O:26])[C@@H:16]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[NH2:17].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:13][O:14][C:15](=[O:26])[C@@H:16]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[NH:17][C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:11]

Komponenten

5

Edukt 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 134565methyl D-tyrosinate hydrochloride

Produkt 1

HCID 54468447n-(2,6-Dichlorobenzoyl)-d-tyrosine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of 2,6-dichlorobenzoylchloride (0.68 mL) in CH2Cl2 (5 mL) was added to a solution of an ice-cold solution of D-tyrosine methyl ester HCl salt (1.0 g) and DIEA (2.26 mL) in CH2Cl2 (15 mL). The mixture was stirred at room temperature for 24 h. The mixture was diluted with CH2Cl2 (50 mL) and washed successively with H2O, 1 N HCl and brine. The organic layer was dried (MgSO4) and evaporated, and the residue was recrystallized from EtOAc and hexanes to yield 1.46 g of N-(2,6-dichlorobenzoyl)-D-tyrosine methyl ester. ESMS: m/z 369 (MH+).

Aufarbeitung

  1. washwashed successively with H2O, 1 N HCl and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customthe residue was recrystallized from EtOAc and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bcaf08c5d8d649d39fd05e7a41426600
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855843B2

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