Water → HCID 11612430, compound

HRID 1865447Notes

Reaction equation

HRID 1865447 reaction equation
[OH-].[Na+].[CH:3]1([CH2:6][O:7][C@@H:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[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]=3)=[CH:16][CH:15]=2)[C:9]([O:11]C)=[O:10])[CH2:5][CH2:4]1.O1CCCC1.CO.O>C(O)(=O)C>[CH:3]1([CH2:6][O:7][C@@H:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[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]=3)=[CH:16][CH:15]=2)[C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67304861HCID 67304861, compound

Product 1

HCID 11612430HCID 11612430, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

21 mg (0.54 mmol) of sodium hydroxide are added to a solution of 86 mg (0.18 mmol) of methyl (S)-2-cyclopropylmethoxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propionate in 2 ml of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred at ambient temperature overnight. 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). 70 mg of 2(S)-cyclopropylmethoxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid are obtained in the form of an oil. Yield=84%.

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-0dfc5d588c944e98b9a3a34c862f5d47
Source dataset
uspto-grants-2009_12
Patent number
US07626054B2

Reaction notes

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