Water → HCID 11626643, compound

HRID 1865450Notes

Reaction equation

HRID 1865450 reaction equation
[OH-].[Na+].[CH2:3]([O:6][C@@H:7]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]([CH3:36])[C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:27])[CH:20]=2)=[CH:15][CH:14]=1)[C:8]([O:10]C)=[O:9])[CH2:4][CH3:5].O1CCCC1.CO.O>C(O)(=O)C>[CH2:3]([O:6][C@@H:7]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]([CH3:36])[C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:27])[CH:20]=2)=[CH:15][CH:14]=1)[C:8]([OH:10])=[O:9])[CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67304789HCID 67304789, compound

Product 1

HCID 11626643HCID 11626643, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

51 mg (1.28 mmol) of sodium hydroxide are added to a solution of 200 mg (0.42 mmol) of methyl (S)-2-propyloxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate in 2 ml of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred overnight at ambient temperature. The reaction is halted by the addition of 2 ml of water and 0.5 ml of acetic acid, and then extraction is carried out with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated and then the residue is chromatographed on silica gel (dichloromethane/methanol 90/10). 147 mg of 2-(S)-propyloxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid are obtained in the form of an oil. Yield=76%.

Workup

  1. extractionextraction
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated
  4. customthe residue is chromatographed on silica gel (dichloromethane/methanol 90/10)

Sources & evidence

ORD record
ord-9b20728ef35742009f30a5f252a78319
Source dataset
uspto-grants-2009_12
Patent number
US07626054B2

Reaction notes

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