Hydrochloric Acid → N-{4-[{3-([tert-butoxycarbonyl)(methyl)amino]propyl}(methyl)carbamoyl]phenyl}-beta-alanine

HRID 446604Notes

Reaction equation

HRID 446604 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:30])[CH2:9][CH2:10][CH2:11][N:12]([CH3:29])[C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[CH:17][CH:16]=1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.C(OCC)(=O)C>C(O)C>[C:1]([O:5][C:6]([N:8]([CH3:30])[CH2:9][CH2:10][CH2:11][N:12]([CH3:29])[C:13]([C:15]1[CH:16]=[CH:17][C:18]([NH:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:19][CH:20]=1)=[O:14])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 66793768Ethyl N-{4-[{3-([tert-butoxycarbonyl)(methyl)amino]propyl}(methyl)carbamoyl]phenyl}-beta-alaninate

Product 1

HCID 66793718N-{4-[{3-([tert-butoxycarbonyl)(methyl)amino]propyl}(methyl)carbamoyl]phenyl}-beta-alanine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (355 mg, 0.84 mmol) obtained in Example 94a was dissolved in ethanol (4 mL), a 1 N aqueous sodium hydroxide solution (1.26 mL, 1.26 mmol) was added, and the mixture was stirred at room temperature for 2.5 hours. After the reaction was completed, a 1 N aqueous hydrochloric acid solution (1.26 mL, 1.26 mmol) was added to the reaction mixture under ice cooling, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give crude N-{4-[{3-([tert-butoxycarbonyl)(methyl)amino]propyl}(methyl)carbamoyl]phenyl}-β-alanine.

Workup

  1. customto separate the layers
  2. customThe resulting organic layer was separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-97502998b8064114a0ec01746b46b09c
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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