Hydrochloric Acid → HCID 56848346, compound

HRID 2405655Notes

Reaction equation

HRID 2405655 reaction equation
[CH2:1]([C:4]1[CH:28]=[CH:27][C:7]([CH2:8][N:9]([CH2:22][C:23]([O:25]C)=[O:24])[C:10](=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[OH-].[Na+].Cl>CO.C(OCC)(=O)C>[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]([CH2:22][C:23]([OH:25])=[O:24])[C:10](=[O:21])[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH3:20])=[CH:16][CH:17]=2)=[CH:27][CH:28]=1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86690146HCID 86690146, compound

Product 1

HCID 56848346HCID 56848346, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(N-(4-propylbenzyl)-2-(4-propylphenyl)acetamido)-acetate (30.0 mg, 0.0786 mmol) was dissolved in 0.5 mL of methanol, and then 100 μL of 20% aqueous sodium hydroxide solution was added, and the reaction mixture was stirred for 2 hours at room temperature. Upon completion of the reaction, the reaction solution was diluted with 2 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 26.4 mg (0.0718 mmol, 91%) 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-c410c1933d6b437fb455963303b24484
Source dataset
uspto-grants-2014_08
Patent number
US08809012B2

Reaction notes

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