Water → HCID 68838279, compound

HRID 660762Notes

Reaction equation

HRID 660762 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])=[CH:4][C:3]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([O:37][CH3:38])=[O:36].O>CN(C=O)C>[CH3:15][Si:13]([CH3:16])([CH3:14])[CH2:12][CH2:11][O:10][C:8](=[O:9])[CH2:7][O:6][C:5]1[CH:17]=[CH:18][C:2]([NH:1][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[C:3]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 866325892-Trimethylsilanylethyl (4-amino-3-benzyloxyphenoxy)acetate

Product 1

HCID 68838279HCID 68838279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2-trimethylsilanylethyl (4-amino-3-benzyloxyphenoxy)acetate (4.56 g, 12.2 mmol) and potassium carbonate (3.37 g, 24.4 mmol) in DMF (25 mL) is added methyl bromoacetate (1.87 g, 12.2 mmol). The mixture is stirred at 60° C. for 1 h then is allowed to cool to RT. It is poured into water and extracted with EtOAc and the organic phase is washed with water (1×), brine (5×), and dried over Na2SO4. The solvent is removed under reduced pressure to afford the title compound which is used directly in the next step.

Workup

  1. temperatureto cool to RT
  2. extractionextracted with EtOAc
  3. washthe organic phase is washed with water (1×), brine (5×)
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-6bfef0f14dcf48e8a57409954bef09ca
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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