Water → HCID 11546938, compound

HRID 1865454Notes

Reaction equation

HRID 1865454 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])[CH:4]=[CH2:5].C1COCC1.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])[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67305114HCID 67305114, compound

Product 1

HCID 11546938HCID 11546938, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

56 mg (1.4 mmol, 3 eq) of sodium hydroxide are added to a solution of 200 mg (0.47 mmol, 1 eq) of methyl (S)-2-allyloxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate in 2 ml of 9/1 THF/methanol. The reaction mixture is stirred at ambient temperature for 3 hours. 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). 152 mg of 2(S)-allyloxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid are obtained in the form of an oil. Yield=78%.

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-b3d646d8930c4e7ab6ff452e90d8e567
Source dataset
uspto-grants-2009_12
Patent number
US07626054B2

Reaction notes

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