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

HRID 1424317Notes

Reaction equation

[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

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 6712144-Bromo-L-phenylalanine

Product 1

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

Procedure

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.

Workup

customEvaporation of the solvent

Sources & evidence

ORD record: ord-89c55b79e431430383c54221e7ef7434
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927534B2

Reaction notes

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