Water → HCID 11612430, compound

HRID 1009223Notes

Reaction equation

HRID 1009223 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-9d594e9f6b83425c815343b6e9c6d783
Source dataset
uspto-grants-2011_07
Patent number
US07973063B2

Reaction notes

Loading…