Reacción #2798

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, tert-butyl ester

hydrochloric acid

→

title compound

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

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONTreat
2. 2
   Otrowith degassed 1N aqueous lithium hydroxide (1.0 mL)
3. 3
   Temperaturato warm gradually over 3 hours
4. 4
   OtroWith the reaction at 0° C.
5. 5
   OtroPartition between methylene chloride and water
6. 6
   Secadodry (Na2SO4)
7. 7
   Otropurify by silica gel chromatography

Procedimiento

Combine 2-[4-(2-Benzoylsulfanyl-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-valeric acid, tert-butyl ester (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 and water, dry (Na2SO4) and purify by silica gel chromatography to give the title compound.

Fuente