Reacción #2813

Ecuación de reacción

2-[4-(2-benzoylsulfanyl-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-valeric acid

hydrochloric acid

→

title compound

Rendimiento 80.8%

2-[4-(2-Mercapto-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-valeric acid

Rendimiento 80.8%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacool in an ice bath
2. 2
   workup.ADDITIONTreat
3. 3
   Otrowith degassed 1N aqueous lithium hydroxide (1.0 mL)
4. 4
   Temperaturato warm gradually over 3 hours
5. 5
   OtroWith the reaction at 0° C.
6. 6
   OtroPartition between methylene chloride (75 mL) and water (25 mL)
7. 7
   Secadodry (Na2SO4)
8. 8
   Otropurify by silica gel chromatography (3:1:0.01 hexane/ethyl acetate/acetic acid

Procedimiento

Dissolve 2-[4-(2-benzoylsulfanyl-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-valeric acid (0.229 mmol) in degassed methanol (3 mL) and cool in an ice bath. Treat with degassed 1N aqueous lithium hydroxide (1.0 mL) and stir, allowing the ice bath to warm gradually over 3 hours. With the reaction at 0° C., acidify with 5% hydrochloric acid. Partition between methylene chloride (75 mL) and water (25 mL), dry (Na2SO4) and purify by silica gel chromatography (3:1:0.01 hexane/ethyl acetate/acetic acid followed by 1:1:0.01 hexane/ethyl acetate/acetic acid to give the title compound as a white solid (84 mg, 80.8%).

Fuente