Reaction #2467945

ord-accdf6f97f42477495e66d1febd6ca08

Reaction equation

O=C(O)C(=O)Cc1ccccc1
2-Oxo-3-phenyl-propionic acid
CNc1nc(-c2ccccc2)cs1
(4-Phenyl-thiazol-2-yl)-methylamine
[BH3-]C#N.[Na+]
NaBH3CN
O=C(O)C(Cc1ccccc1)NCc1nc(-c2ccccc2)cs1
product
Yield 62.1%
O=C(O)C(Cc1ccccc1)NCc1nc(-c2ccccc2)cs1
3-Phenyl-2-[(4-phenyl-thiazol-2-ylmethyl)-amino]-propionic acid
Yield 62.1%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe product was purified by HPLC

Procedure

To a solution of 2-Oxo-3-phenyl-propionic acid (1.6 mmol, 264 mg) and (4-Phenyl-thiazol-2-yl)-methylamine (1.0 mmol, 190 mg) in MeOH (4 mL), is added NaBH3CN (2.0 mmol, 1N in THF). The pH was then adjusted at 6 with 1M HClaq. The mixture was stirred at room temperature for 3 days. The product was purified by HPLC to give the pure product (210 mg, 62%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08257931B2uspto-grants-2012_09