Pyridine → Ethyl 2-(3-Aminocarbonylmethylphenoxy)-2-methylpropionate

HRID 480712Notes

Reaction equation

HRID 480712 reaction equation
[CH2:1]([O:3][C:4]([C:6]([CH3:19])([O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16](O)=[O:17])[CH:12]=[CH:13][CH:14]=1)[CH3:7])=[O:5])[CH3:2].[N:20]1C=CC=CC=1.C(=O)([O-])O.[NH4+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(#N)C>[NH2:20][C:16]([CH2:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][C:6]([CH3:19])([CH3:7])[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 187665702-(3-((1-Ethoxy-2-methyl-1-oxopropan-2-yl)oxy)phenyl)acetic acid

Product 1

HCID 18766455Ethyl 2-(3-Aminocarbonylmethylphenoxy)-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(1-Ethoxycarbonyl-1-methylethoxy)phenylacetic acid (532 mg, 0.2 mmol) was dissolved in acetonitrile (3 mL). Subsequently, pyridine (0.1 mL, 1.24 mmol) and ammonium hydrogencarbonate (206 mg, 2.6 mmol) were added thereto, and the mixture was stirred for 10 minutes at room temperature. Thereafter, di-tert-butyl dicarbonate [Boc2O (597.2 mL, 2.6 mmol)] was added thereto, and the mixture was stirred for 14 hours. The reaction mixture was concentrated under reduced pressure, and the resultant concentrate was added to water, followed by extraction with chloroform. Subsequently, washing was performed sequentially with 1M hydrochloric acid and saturated brine. The resultant mixture was subjected to drying over magnesium sulfate, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound was obtained (524 mg, 0.198 mmol, 98.8%).

Workup

  1. stirringthe mixture was stirred for 14 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. concentrationthe resultant concentrate
  4. additionwas added to water
  5. extractionfollowed by extraction with chloroform
  6. washSubsequently, washing
  7. dry with materialto drying over magnesium sulfate, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound
  8. customwas obtained (524 mg, 0.198 mmol, 98.8%)

Sources & evidence

ORD record
ord-c2970372a8794d82a4e30ae362601ae9
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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