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

HRID 1393097Notes

Reaction equation

HRID 1393097 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/aqueous 10% KHSO4, twofold extraction with EtOAc, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/EtOAc=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. extractionice/aqueous 10% KHSO4, twofold extraction with EtOAc
  4. washwashing with water and brine
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-97ade6e75c424404b07eab39887d6962
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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