Water → HCID 11591779, compound

HRID 250925Notes

Reaction equation

HRID 250925 reaction equation
[OH-].[Na+].[CH2:3]([NH:10][C:11](=[O:41])[N:12]([C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[CH:22][C:21]=2[O:32][CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].O>C(O)(=O)C>[CH2:3]([NH:10][C:11](=[O:41])[N:12]([C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][C:21]=2[O:32][CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67272850HCID 67272850, compound

Product 1

HCID 11591779HCID 11591779, compoundYield 2.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

630 mg (1.56 mmol, 2 eq) of sodium hydroxide are added to a solution of 420 mg (0.78 mmol, 1 eq) of methyl 3-[3′-(3-heptyl-1-methylureido)-2-(2-morpholin-4-ylethoxy)biphenyl-4-yl]propanoate in 8 ml of 8/1/1 tetrahydrofuran/methanol/water. The reaction mixture is stirred for 4 hours at room temperature. The reaction medium is hydrolyzed with water and acetic acid and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (40/60 heptane/ethyl acetate) and then on preparative HPLC. 10 mg of 3-[3′-(3-heptyl-1-methylureido)-2-(2-morpholin-4-ylethoxy)biphenyl-4-yl]propanoic acid are obtained in oil form. Yield=2%

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvents are evaporated off
  5. customthe residue is then chromatographed on silica gel (40/60 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-0bcc4ff846fb4d8e8e3177541a0a7dac
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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