Potassium Carbonate → (R)-4-(2-t-Butoxycarbonylaminopropyl)phenoxyacetic acid, methyl ester

HRID 1529Notes

Reaction equation

HRID 1529 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:16])=[CH:10][CH:9]=1.Br[CH2:26][C:27]([O:29][CH3:30])=[O:28]>CC(C)=O>[C:20]([O:19][C:18]([NH:17][C@H:15]([CH3:16])[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:9][CH:10]=1)=[O:24])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 59909921(R)-2-(4-Hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester

Product 1

HCID 86752192(R)-4-(2-t-Butoxycarbonylaminopropyl)phenoxyacetic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (1.95 g, 14.2 mMol) was added to a solution of (R)-2-(4-hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester (2.96 g, 11.8 mMol) in acetone (50 ml) at room temperature under argon. Methyl bromoacetate (1.81 g, 11.8 mMol) was added dropwise and the reaction mixture was heated at reflux for 3 hours. The solvent was removed under reduced pressure and the residue was taken into ethyl acetate and washed with water (2×30 ml). The organic extracts were dried with sodium sulfate and the solvent evaporated in vacuo. The crude product was purified by chromatography on Kieselgel 60 (eluting with 20% ethyl acetate in pentane) to give the title compound as an oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was removed under reduced pressure
  4. washwashed with water (2×30 ml)
  5. dry with materialThe organic extracts were dried with sodium sulfate
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by chromatography on Kieselgel 60 (eluting with 20% ethyl acetate in pentane)

Sources & evidence

ORD record
ord-1f90df0f79374e948d81d55edfef11d9
Source dataset
uspto-grants-1998_03
Patent number
US05726165

Reaction notes

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