4-methylpentan-2-amine

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

Procedure: The mixture of 1-((2′-(tert-butoxycarbonyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-5-carboxylic acid (45 mg, 0.105 mmol), 4-methylpentan-2-amine (12.7 mg, 0.126 mmol), HATU (78 mg, 0.315 mmol) and DIPEA (27 mg, 0.315 mmol) in 10 mL of DCM was stirred at RTovernight. Then the solvent was removed under the reduced pressure to give the residue which was purified with prep-TLC (hexane/EtOAc=1/1, silica gel) to give the title compound. Then the solvent was removed under the reduced pressure to give the residue which was purified with prep-TLC (hexane/EtOAc=1/1, silica gel)

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

Procedure: The title compound was prepared from (2S)-3-(4-carboxymethoxy-phenyl)-2-methoxy-propionic acid ethyl ester (PREPARATION 3, step 2) and 1,3-dimethyl-butylamine via the same procedure used for the preparation of (2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)-propionic acid (Example 1, step 3) to produce a colorless oil. MS (ES) for C18H27NO5 [M−H]−: 336. to produce a colorless oil

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

Procedure: The mixture of 1-((2′-(tert-butoxycarbonyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-5-carboxylic acid (45 mg, 0.105 mmol), 4-methylpentan-2-amine (12.7 mg, 0.126 mmol), HATU (78 mg, 0.315 mmol) and DIPEA (27 mg, 0.315 mmol) in 10 mL of DCM was stirred at RTovernight. Then the solvent was removed under the reduced pressure to give the residue which was purified with prep-TLC (hexane/EtOAc=1/1, silica gel) to give the title compound. Then the solvent was removed under the reduced pressure to give the residue which was purified with prep-TLC (hexane/EtOAc=1/1, silica gel)