Hydrochloric Acid → HCID 56848396, compound

HRID 2405658Notes

Reaction equation

HRID 2405658 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([N:13]([CH2:23][C:24]([O:26]C)=[O:25])[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO.C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([N:13]([CH2:23][C:24]([OH:26])=[O:25])[CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86690147HCID 86690147, compound

Product 1

HCID 56848396HCID 56848396, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(5-phenyl-N-(3-phenylpropyl)pentanamido)acetate (34.2 mg, 0.0931 mmol) was dissolved in 0.5 mL of methanol and then 100 μL of 20% aqueous sodium hydroxide solution was added. The reaction mixture was then stirred for 2 hours at room temperature. Upon completion of the reaction, the reaction solution was diluted with 3 mL of ethyl acetate and neutralized by adding 200 μL of 10% aqueous hydrogen chloride solution. After removing water with anhydrous magnesium sulfate and filtering out the precipitate, the resulting solution was concentrated by distillation under reduced pressure and purified by column chromatography to obtain 26.2 mg (0.0741 mmol, 80%) of the desired compound.

Workup

  1. customUpon completion of the reaction
  2. customAfter removing water with anhydrous magnesium sulfate
  3. filtrationfiltering out the precipitate
  4. concentrationthe resulting solution was concentrated by distillation under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-863c8e99117a4bd898ec09c47927b504
Source dataset
uspto-grants-2014_08
Patent number
US08809012B2

Reaction notes

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