methyl (2S)-2-amino-3-(4-bromophenyl)propanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.0 g (2.5 mmol) of resin-bound naphthoic acid obtained in Example 1 was reacted with 1.95 g (7.5 mmol) of (2S)-Amino-3-(4-bromophenyl)-propionic acid methyl ester as described in the general procedure A to give resin-bound 2-(S)-(3-Hydroxy-naphthalene-2-carbonyl)-amino-3-(4-bromophenyl)-propionic acid methyl ester.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.0 g (2.5 mmol) of resin-bound naphthoic acid obtained in Example 1 was reacted with 1.95 g (7.5 mmol) of (2S)-Amino-3-(4-bromophenyl)-propionic acid methyl ester as described in the general procedure A to give resin-bound 2-(S)-(3-Hydroxy-naphthalene-2-carbonyl)-amino-3-(4-bromophenyl)-propionic acid methyl ester.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 500 mg (1.55 mmol) of 7-(4-tert-butylphenoxy)-isoquinoline-3-carboxylic acid (Example 371) was reacted with 441 mg (1.7 mmol) of (2S)-amino-3-(4-bromo-phenyl)-propionic acid methyl ester as described in general procedure A. The crude product was purified by flash column chromatography on silica using 8:2 hexane/ethyl acetate as eluent, to afford 830 mg of the title compound as a white solid. The crude product was purified by flash column chromatography on silica using 8:2 hexane/ethyl acetate as eluent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. Evaporation of the solvent