Hydrochloric Acid → HCID 11259669, compound

HRID 1865746Notes

Reaction equation

HRID 1865746 reaction equation
[CH3:1][C@@H:2]([C:27]([CH3:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:28])[C:3]([NH:5][C@@H:6]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:7]([N:9]([CH3:22])[C@@H:10]([CH:19]([CH3:21])[CH3:20])/[CH:11]=[C:12](\[CH3:18])/[C:13]([O:15]CC)=[O:14])=[O:8])=[O:4].O1CCCC1.O.[OH-].[Li+].Cl>CO.O>[CH3:1][C@@H:2]([C:27]([CH3:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:28])[C:3]([NH:5][C@@H:6]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:7]([N:9]([CH3:22])[C@@H:10]([CH:19]([CH3:20])[CH3:21])/[CH:11]=[C:12](\[CH3:18])/[C:13]([OH:15])=[O:14])=[O:8])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69019295HCID 69019295, compound

Product 1

HCID 11259669HCID 11259669, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Ethyl (E,4S)-4-[((2S)-2-{[(2S)-2,3-dimethyl-3-phenylbutanoyl]amino}-3,3-dimethylbutanoyl)(methyl)amino]-2,5-dimethyl-2-hexenoate (0.17 g, 0.35 mmol, from Example 91) is dissolved in methanol (1.2 mL) and tetrahydrofuran (1.2 mL) and cooled to 0° C. (ice water bath). To this solution is added water (0.6 mL) and aqueous lithium hydroxide monohydrate (30 mg, 0.70 mmol). The cooling bath is removed, and the resulting mixture is stirred at 50° C. for 15 hours. Solvents are removed in vacuo to provide a beige foam, which is then dissolved in water. The solution is acidified to pH 1 with 10% aqueous hydrochloric acid solution and then extracted thrice with ethyl acetate. The combined extracts are washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, decanted, and concentrated under reduced pressure to afford a white solid (0.16 g, 100%). MS (ES+): (M+H)=459.0

Workup

  1. customThe cooling bath is removed
  2. customSolvents are removed in vacuo
  3. customto provide a beige foam, which
  4. extractionextracted thrice with ethyl acetate
  5. washThe combined extracts are washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customdecanted
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1793015cfcee404fa622ff403e236f9f
Source dataset
uspto-grants-2009_12
Patent number
US07626023B2

Reaction notes

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