Réaction #2798

Équation de réaction

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

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONTreat
2. 2
   Autrewith degassed 1N aqueous lithium hydroxide (1.0 mL)
3. 3
   Températureto warm gradually over 3 hours
4. 4
   AutreWith the reaction at 0° C.
5. 5
   AutrePartition between methylene chloride and water
6. 6
   Séchagedry (Na2SO4)
7. 7
   Autrepurify by silica gel chromatography

Mode opératoire

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.

Source