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

HRID 1060402

Reaktionsgleichung

Reaktionsgleichung von HRID 1060402
[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-224f3b68652a444587bea5dbc305a64d
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521666B1

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