Hydrochloric Acid → 3-(4-Acetoxy-2,6-dimethyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

Reaktionsgleichung

[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([OH:21])=[CH:16][C:15]=1[CH3:22])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:25](OC(=O)C)(=[O:27])[CH3:26].Cl>>[C:25]([O:21][C:17]1[CH:16]=[C:15]([CH3:22])[C:14]([CH2:13][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([OH:12])=[O:11])=[C:19]([CH3:20])[CH:18]=1)(=[O:27])[CH3:26]

Komponenten

Edukt 4

HCID 313Hydrochloric Acid

HCID 7918Acetic Anhydride

HCID 14798Sodium Hydroxide

HCID 13656656Boc-L-2,6-Dimethyltyrosine

Produkt 1

HCID 221476663-(4-Acetoxy-2,6-dimethyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

Versuchsvorschrift

To a solution of 0.77 g (2.5 mmol) of 2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid and 3 mL of 3N sodium hydroxide solution, cooled in an ice bath, was added 0.89 mL (9.4 mmol) of acetic anhydride dropwise over about 30 seconds. After stirring for 2 hours, the mixture was acidified with addition of 4.5 mL of 2N hydrochloric acid. The mixture was extracted twice with ethyl acetate. The combined organics were dried over magnesium sulfate and concentrate to a clear oil. The title product was used for the next reaction without further purification.