Sodium Hydroxide → 3-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propionic acid

HRID 220263

Reaction equation

HRID 220263 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[N:7]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1.[OH-].[Na+]>C(O)C>[C:11]1([C:9]2[N:10]=[C:6]([CH2:5][CH2:4][C:3]([OH:31])=[O:2])[N:7]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])[C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 684117713-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propionic acid methyl ester

Product 1

HCID 684143723-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propionic acidYield 94.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

150 mg of 3-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propionic acid methyl ester were dissolved in 1 mL of ethanol and treated with 0.7 mL of a 1M aq. solution of sodium hydroxide. The mixture was partitioned between water and Et2O. The aq. layer was separated, acidified with 25%-HCl and extracted with DCM. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo to give 137 mg of 3-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propionic acid the product as a white solid.

Workup

  1. customThe mixture was partitioned between water and Et2O
  2. customThe aq. layer was separated
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over anh. Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c55cd5a7d824a9bbde270638954d690
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Linked notes

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