Sodium Hydroxide → 3-[2-(3-Chloropropoxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid

HRID 250852Notes

Reaction equation

HRID 250852 reaction equation
[OH-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([CH2:14][CH2:15][C:16]([O:18]C)=[O:17])[CH:11]=[CH:10][C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]([CH3:37])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:28])[CH:21]=1>CO>[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:11]=[CH:10][C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]([CH3:37])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:28])[CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67272211Methyl 3-[2-(3-chloropropoxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

Product 1

HCID 115767593-[2-(3-Chloropropoxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acidYield 6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

31 mg (0.773 mmol, 1 eq) of sodium hydroxide are added to a solution of 389 mg (0.773 mmol, 1 eq) of methyl 3-[2-(3-chloropropoxy)-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate in 10 ml of methanol. The reaction mixture is stirred at room temperature for 18 hours. The reaction medium is evaporated to dryness, taken up in water, acidified with 2N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over magnesium sulfate. The solvent is evaporated off and the oil obtained is chromatographed on silica gel (10 g FlashSmart column) eluted with 98/2 dichloromethane/methanol. The product is crystallized from heptane, the filtrate is evaporated and 21 mg of 3-[2-(3-chloropropoxy)-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid are obtained in the form of a whitish oil. Yield=6%

Workup

  1. customThe reaction medium is evaporated to dryness
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is evaporated off
  6. customthe oil obtained
  7. customis chromatographed on silica gel (10 g FlashSmart column)
  8. washeluted with 98/2 dichloromethane/methanol
  9. customThe product is crystallized from heptane
  10. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-1759b19ce64748959d64a4fdb668204c
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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