Potassium Carbonate → [2-(t-Butoxycarbonylmethyl-amino)-phenyl]-acetic acid methyl ester

HRID 1592019Notes

Reaction equation

HRID 1592019 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 5743389Methyl 2-aminobenzeneacetate

Product 1

HCID 67139746[2-(t-Butoxycarbonylmethyl-amino)-phenyl]-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The title B compound, (2-amino-phenyl) acetic acid methyl ester (4.2 g, 25.4 mmol) is dissolved in DMF (30 mL). Powdered potassium carbonate (8.78 g, 63.5 mmol) and t-butyl bromoacetate (4.12 mL, 27.9 mmol) are added and the reaction is stirred at room temperature for 18 h and then at 50° C. for 1 h. The reaction is diluted with water (300 mL) and extracted with EtOAc (2×200 mL). Combined EtOAc layers are washed with water (2×100 mL) then brine (100 mL), dried over anhydrous MgSO4, filtered and concentrated to give a viscous brown oil. This residue is chromatographed on a 110 g silica gel RediSep (Isco Inc.) column with a 30 mL/min gradient elution of 10:90 (EtOAc:hexane) to 25:75 over 30 min. Fractions containing product are combined and evaporated to yield [2-(t-butoxy-carbonylmethyl-amino)-phenyl]-acetic acid methyl ester as a clear amber oil: [M+1]+=280.

Workup

  1. waitat 50° C. for 1 h
  2. extractionextracted with EtOAc (2×200 mL)
  3. washCombined EtOAc layers are washed with water (2×100 mL)
  4. dry with materialbrine (100 mL), dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a viscous brown oil
  8. customThis residue is chromatographed on a 110 g silica gel RediSep (Isco Inc.) column with a 30 mL/min gradient elution of 10:90 (EtOAc:hexane) to 25:75 over 30 min
  9. additionFractions containing product
  10. customevaporated

Sources & evidence

ORD record
ord-224f4aebfd4041fc890ce2ec0da7408b
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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