Methyl iodide → HCID 69220575, compound

HRID 1393072Notes

Reaction equation

HRID 1393072 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][C:8]=1[CH3:21])[CH3:2].[H-].[Na+].[CH3:25]I.OS([O-])(=O)=O.[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH3:25])=[CH:9][C:8]=1[CH3:21])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 54295890HCID 54295890, compound

Product 1

HCID 69220575HCID 69220575, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled and stirred solution of (4-tert-butoxycarbonylamino-2-methyl-phenoxy)-acetic acid ethyl ester (3.09, 10 mmol) in DMF (30 ml) was added within 10 min NaH (55% in oil, 0.65 g, 15 mmol) and after 1 h, CH3I (4.98 ml, 80 mmol). The reaction was warmed up over night to RT, neutralized at 0° C. 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 3.46 g (quantitative) of [4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid ethyl ester containing ca 20% (1H-NMR) of [4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl ester, MS: 323 (M, ethyl ester) and 309 (M, methyl ester).

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-b8c8d2a1a45b4cf78f4dfef0bdd65bb9
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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