Hydrochloric Acid → 2-(4-{2-[1-(4-Methanesulfonyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 1985232Notes

Reaction equation

HRID 1985232 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:24])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH:17]2[CH2:21][NH:20][C:19](=[O:22])[N:18]2[CH3:23])=[CH:10][CH:9]=1)[CH3:6])[CH3:2].[H-].[Na+].[CH3:28][S:29]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Cl)=[CH:34][CH:33]=1)(=[O:31])=[O:30].Cl>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:25])[C:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][CH:17]2[CH2:21][N:20]([CH2:36][C:35]3[CH:34]=[CH:33][C:32]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:39][CH:38]=3)[C:19](=[O:22])[N:18]2[CH3:23])=[CH:12][CH:13]=1)([CH3:24])[CH3:6])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1235301-(Chloromethyl)-4-methanesulfonylbenzeneHCID 577191912-Methyl-2-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenoxy}-propionic acid ethyl ester

Product 1

HCID 577190632-(4-{2-[1-(4-Methanesulfonyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl esterYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-methyl-2-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenoxy}-propionic acid ethyl ester (0.143 g, 0.408 mmol) in dry DMF (4 mL) was treated a 60% suspension of NaH (0.033 g, 0.825 mmol) and the resultant mixture was stirred at room temperature for 20 minutes under N2. The reaction mixture was cooled to 0° C. and then treated with p-methylsulfonylbenzyl chloride and then warmed to room temperature and stirred for 16 h. The reaction was acidified with aqueous 1 N HCl (4 mL), diluted with water and extracted with Et2O. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford crude product that was purified by column chromatography using a gradient of 4:1 to 1:1 hexanes:acetone to afford 0.090 g (42%) 2-(4-{2-[1-(4-methanesulfonyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester. Rf=0.40 (1:1 hexanes:acetone) MS (ES+) Calc'd for C26H35N2O7S (M+1) 518. Found m/z 518 (100%). 1H NMR.

Workup

  1. temperaturewarmed to room temperature
  2. extractionextracted with Et2O
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto afford crude product that
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6e030937e3804f10ba978d2de7fcd538
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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