Methyl iodide → 4-(tert-Butoxycarbonyl-methyl-amino)-2-(3-methoxy-propyl)-phenoxy-acetic acid ethyl ester

HRID 1242281Notes

Reaction equation

HRID 1242281 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[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[CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH3:2].[H-].[Na+].[CH3:29]I>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:29])=[CH:9][C:8]=1[CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 670721874-tert-Butoxycarbonylamino-2-(3-methoxy-propyl)-phenoxy-acetic acid ethyl ester

Product 1

HCID 670721854-(tert-Butoxycarbonyl-methyl-amino)-2-(3-methoxy-propyl)-phenoxy-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2.21 g (6.01 mmol) of the above prepared [4-tert-butoxycarbonylamino-2-(3-methoxy-propyl)-phenoxy]-acetic acid ethyl ester, dissolved in 18 ml of abs. DMF, was added at 0° C. 0.313 g of NaH (60% in mineral oil, 1.3 eq.). 5 Min. later, 0.75 ml (2 eq.) of MeI was added and the reaction allowed to proceed for 10 Min. at 0° C. and for 1 h at ambient temperature. Pouring onto crashed ice/KHSO4 solution, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=8/2), yielded 1.55 g of the title compound as light yellow oil.

Workup

  1. dissolutiondissolved in 18 ml of abs
  2. additionPouring
  3. extractionextraction with AcOEt
  4. washwashing with water and brine
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-4621a43c5ecd4422b9a996bacc0b14a4
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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