Reacción #1269865

Ecuación de reacción

HCl

suspension

4-(2-{[5-(3-Hydroxy-propylamino)-2-phenyl-thiazole-4-carbonyl]-amino}-acetyl)-piperazine-1-carboxylic acid butyl ester

diacetoxyiodobenzene

2,2,6,6-tetramethylpiperidine-1-oxyl

→

desired product

Rendimiento 31.1%

4-(2-{[5-(2-Carboxy-ethylamino)-2-phenyl-thiazole-4-carbonyl]-amino}-acetyl)-piperazine-1-carboxylic acid butyl ester

Rendimiento 31.1%

Disolventes

H2O

H2O CH3CN

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with EtOAc (3×5 mL) The combined organic layers
2. 2
   Secadowere dried over Na2SO4
3. 3
   Concentraciónconcentrated to dryness
4. 4
   OtroPurification by CC (CH2Cl2/MeOH 97:3)

Procedimiento

To a suspension of Example 27 (25 mg) in H2O/CH3CN (0.2 mL, 1:1) was added at 0° C. diacetoxyiodobenzene (35 mg) and 2,2,6,6-tetramethylpiperidine-1-oxyl (3 mg), and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was diluted with H2O, acidified with aq. HCl (1M, 0.5 mL) and extracted with EtOAc (3×5 mL) The combined organic layers were dried over Na2SO4 and concentrated to dryness. Purification by CC (CH2Cl2/MeOH 97:3) gave 8 mg of the desired product.

Fuente