Pyridine → tert-Butyl 2-[3-(aminocarbonylmethyl)phenoxy]-2-methylpropionate

HRID 480709Notes

Reaction equation

HRID 480709 reaction equation
[C:1]([O:5][C:6]([C:8]([CH3:21])([O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18](O)=[O:19])[CH:14]=[CH:15][CH:16]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:22]1C=CC=CC=1.C(=O)([O-])O.[NH4+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(#N)C>[NH2:22][C:18]([CH2:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:8]([CH3:21])([CH3:9])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:19]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 187664143-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic Acid

Product 1

HCID 18766448tert-Butyl 2-[3-(aminocarbonylmethyl)phenoxy]-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic acid (2.0 g, 6.79 mmol) is dissolved in acetonitrile (15 mL). Subsequently, pyridine (0.34 mL, 4.22 mmol) and ammonium hydrogencarbonate (699 mg, 8.84 mmol) were added thereto, and the mixture was stirred for 10 minutes at room temperature. Thereafter, di-tert-butyl dicarbonate [Boc2O (2.03 mL, 8.84 mmol)] was added thereto, and the resultant mixture was stirred for 14 hours. The reaction mixture was concentrated under reduced pressure. Thereafter, the resultant concentrate was added to water, and the mixture was extracted with chloroform, followed by washing 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 (1.07 g, 3.65 mmol, 53.6%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationThereafter, the resultant concentrate
  3. additionwas added to water
  4. extractionthe mixture was extracted with chloroform
  5. washby washing sequentially with 1M hydrochloric acid and saturated brine
  6. 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
  7. customwas obtained (1.07 g, 3.65 mmol, 53.6%)

Sources & evidence

ORD record
ord-3b4e6c4b8375471aabb9d7fc6c585f65
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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