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

HRID 1264547Notes

Reaction equation

HRID 1264547 reaction equation
C([S:9][CH:10]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:11]([NH:13][CH:14]1[C:20](=[O:21])[N:19]([CH:22]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:23]([OH:25])=[O:24])[CH2:18][C:17]2[CH:30]=[CH:31][CH:32]=[CH:33][C:16]=2[CH2:15]1)=[O:12])(=O)C1C=CC=CC=1.Cl>CO>[SH:9][CH:10]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:11]([NH:13][CH:14]1[C:20](=[O:21])[N:19]([CH:22]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:23]([OH:25])=[O:24])[CH2:18][C:17]2[CH:30]=[CH:31][CH:32]=[CH:33][C:16]=2[CH2:15]1)=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 186125262-(4-(2-Benzoylsulfanyl-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid

Product 1

HCID 186125182-(4-(2-Mercapto-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acidYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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 1M 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%).

Workup

  1. temperaturecool in an ice bath
  2. additionTreat
  3. customwith degassed 1M aqueous lithium hydroxide (1.0 mL)
  4. temperatureto warm gradually over 3 hours
  5. customWith the reaction at 0° C.
  6. customPartition between methylene chloride (75 mL) and water (25 mL)
  7. dry with materialdry (Na2SO4)
  8. custompurify by silica gel chromatography (3:1:0.01 hexane/ethyl acetate/acetic acid

Sources & evidence

ORD record
ord-b38ab382a80649c7983424914204eccb
Source dataset
uspto-grants-2003_04
Patent number
US06544980B2

Reaction notes

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