Hydrochloric Acid → Methyl (2S)-2-amino-3-(4-bromophenyl)propanoate

HRID 1424317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424317
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1.Cl.[CH3:15]O>>[NH2:1][C@H:2]([C:11]([O:13][CH3:15])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Br:10])=[CH:8][CH:9]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6712144-Bromo-L-phenylalanine

Produkt 1

HCID 24720903Methyl (2S)-2-amino-3-(4-bromophenyl)propanoate

Versuchsvorschrift

1.0 g (4.01 mmol) H-Phe(4-Br)—OH were refluxed in 20 ml methanol with 2.1 ml HCl (4 M in 1,4-dioxane) over night. Evaporation of the solvent gave H-Phe(4-Br)—OMe*HCl as white solid. 1.0 g (3.4 mmol) of this hydrochloride and 1.7 ml (10.2 mmol) DIPEA were suspended in 8 ml THF and 0.41 ml (3.4 mmol) 2,4,6-trimethylbenzoyl chloride were added dropwise at 0° C. After 18 h at room temperature the reaction was quenched with water and the solvent was removed. The residue was suspended in ethyl acetate, washed with saturated Na2SO4 and brine to give compound (13) as an oil.

Aufarbeitung

  1. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-89c55b79e431430383c54221e7ef7434
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927534B2

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