Methyl iodide → [4-(Tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl ester

HRID 1393107Notes

Reaction equation

HRID 1393107 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][C:7]=1[CH3:20].[H-].[Na+].[CH3:24]I.OS([O-])(=O)=O.[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH3:24])=[CH:8][C:7]=1[CH3:20]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 67072259HCID 67072259, compound

Product 1

HCID 67072167[4-(Tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl esterYield 108.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled and stirred solution of (4-tert-butoxycarbonylamino-2-methyl-phenoxy)-acetic acid methyl ester (22.8 g, 77 mmol) in DMF (230 ml) was added within 10 min NaH (3.7 g, 55% in oil, 85 mmol) and after 1 h, CH3I (14.5 ml, 232 mmol). The reaction was stirred at 0° C. for 2 h, neutralized with aqueous 10% KHSO4 and extracted with aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 25.8 g of [4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl ester, MS: 310 (MH+).

Workup

  1. extractionextracted with aqueous 10% KHSO4/Et2O (3×)
  2. washThe organic phases were washed with aqueous 10% NaCl
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-b023d9b6a54f436e9f7acb7fbd681ec4
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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