Methyl iodide → HCID 77078189, compound

HRID 1184296Notes

Reaction equation

HRID 1184296 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=O)C(F)(F)F.CI.[H-].[Na+]>C1COCC1>[CH3:19][NH:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][C:3]([OH:25])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86668692HCID 86668692, compound

Product 1

HCID 77078189HCID 77078189, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under an inert atmosphere of argon, in a round bottom flask, with magnetic stirring, 120.1 mg of 3-[2-(2-{2-[2-(2,2,2-trifluoro-acetylamino)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-propionic acid methyl ester, 1 ml of anhydrous THF and 59.8 μl of CH3I and successively introduced. The reaction medium is cooled with a ice/water bath at about 0° C., and 16.1 mg of NaH (50% pure in oil) is slowly added by small portions. After 15 min at 0° C., and 1 hr at RT, the crude reaction medium is concentrated to dryness under RP, and diluted with 0.5 ml of THF and 0.8 ml of water. At RT, 30.6 mg of LiOH is then added to the reaction medium. The crude reaction medium is kept 2 hrs at RT, 16 hrs at −20° C., and then purified by flash-chromatography on 30 g of C18-grafted silica gel (gradient of elution water:acetonitrile from 95:5 to 5:95 by volume). After concentration of fractions containing the desired product under RP, 115.3 mg of 3-(2-{2-[2-(2-methylamino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid are obtained in the form of a yellow oil.

Workup

  1. custom1 hr at RT, the crude reaction medium
  2. concentrationis concentrated to dryness under RP
  3. additiondiluted with 0.5 ml of THF and 0.8 ml of water
  4. additionAt RT, 30.6 mg of LiOH is then added to the reaction medium
  5. customThe crude reaction medium
  6. waitis kept 2 hrs at RT, 16 hrs at −20° C.
  7. custompurified by flash-chromatography on 30 g of C18-grafted silica gel (gradient of elution water:acetonitrile from 95:5 to 5:95 by volume)
  8. additionAfter concentration of fractions containing the desired product under RP, 115.3 mg of 3-(2-{2-[2-(2-methylamino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid
  9. customare obtained in the form of a yellow oil

Sources & evidence

ORD record
ord-cd62ddd9d806402a85c3345993eb2a9b
Source dataset
uspto-grants-2014_03
Patent number
US08668910B2

Reaction notes

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