Reaktion #2798

Reaktionsgleichung

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

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTreat
2. 2
   Sonstigewith degassed 1N aqueous lithium hydroxide (1.0 mL)
3. 3
   Temperaturto warm gradually over 3 hours
4. 4
   SonstigeWith the reaction at 0° C.
5. 5
   SonstigePartition between methylene chloride and water
6. 6
   Trocknendry (Na2SO4)
7. 7
   Sonstigepurify by silica gel chromatography

Vorschrift

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.

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