Hydrochloric Acid → 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

HRID 2702Notes

Reaction equation

HRID 2702 reaction equation
C([S:9][CH:10]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:11]([NH:13][CH:14]1[C:20](=[O:21])[N:19]([CH:22]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][C:17]2[CH:34]=[CH:35][CH:36]=[CH:37][C:16]=2[CH2:15]1)=[O:12])(=O)C1C=CC=CC=1.Cl>CO>[SH:9][CH:10]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:11]([NH:13][CH:14]1[C:20](=[O:21])[N:19]([CH:22]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:18][C:17]2[CH:34]=[CH:35][CH:36]=[CH:37][C:16]=2[CH2:15]1)=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 865855112-(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

Product 1

HCID 867523082-[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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. additionTreat
  2. customwith degassed 1N aqueous lithium hydroxide (1.0 mL)
  3. temperatureto warm gradually over 3 hours
  4. customWith the reaction at 0° C.
  5. customPartition between methylene chloride and water
  6. dry with materialdry (Na2SO4)
  7. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-c24bf49608274542bccfffbad5927301
Source dataset
uspto-grants-1998_03
Patent number
US05731306

Reaction notes

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