Methyl 3-amino-4-hydroxybenzoate → HCID 58001321, compound

HRID 1945379Notes

Reaction equation

HRID 1945379 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([NH2:26])[CH:20]=1.C(=O)(O)[O-].[Na+]>C[Si](OP(=O)=O)(C)C>[CH3:16][O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([NH:26][C:11](=[O:13])[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:15][CH:14]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 10815Methyl 3-amino-4-hydroxybenzoateHCID 157182-(4-Tert-butylphenoxy)acetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 58001321HCID 58001321, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 16133246Trimethyl(phosphooxy)silaneSolvent

Procedure

(4-tert-butyl-phenoxy)-acetic acid (200 mg, 0.96 mmol) and 3-amino-4-hydroxy-benzoic acid methyl ester (240.7 mg, 1.44 mmol) were dissolved in PPSE (3 mL), and reacted for 2.5 h at 140° C. After saturated sodium bicarbonate aqueous solution was added, organic phase was washed with 10% HCl and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (n-Hexane:Ethyl acetate:MeOH=15:3:1) to give 3-[2-(4-tert-butyl-phenoxy)-acetyl-amino]-4-hydroxy-benzoic acid methyl ester as an orange solid (350 mg, 89% yield).

Workup

  1. customreacted for 2.5 h at 140° C
  2. washorganic phase was washed with 10% HCl and brine
  3. dry with materialThe organic phase was dried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-Hexane:Ethyl acetate:MeOH=15:3:1)

Sources & evidence

ORD record
ord-b04da394e60d45749d7c46b99d3ea6a6
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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