Sodium Hydroxide → 3-[3'-(3-Heptyl-1-methylureido)-2-(2-methoxyethoxy)biphenyl-4-yl]propanoic acid

HRID 250848Notes

Reaction equation

[OH-].[Na+].[CH2:3]([NH:10][C:11](=[O:37])[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][O:35][CH3:36])[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>CO>[CH2:3]([NH:10][C:11](=[O:37])[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][O:35][CH3:36])[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Conditions

Temperature: 50 °C

Procedure

278 mg (6.95 mmol, 10 eq) of sodium hydroxide are added to a solution of 337 mg (0.695 mmol, 1 eq) of methyl 3-[3′-(3-heptyl-1-methylureido)-2-(2-methoxyethoxy)biphenyl-4-yl]propanoate in 10 ml of methanol. The reaction mixture is heated at 50° C. for 2 hours. The reaction medium is evaporated to dryness, taken up in water, acidified with 2N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over magnesium sulfate. The solvent is evaporated off and the oil obtained is chromatographed on silica gel (10 g FlashSmart column) eluted with ethyl acetate. 274 mg of 3-[3′-(3-heptyl-1-methylureido)-2-(2-methoxyethoxy)biphenyl-4-yl]propanoic acid are obtained in the form of a whitish oil. Yield=84%

Workup

customThe reaction medium is evaporated to dryness
extractionextracted with ethyl acetate
washwashed with water
dry with materialdried over magnesium sulfate
customThe solvent is evaporated off
customthe oil obtained
customis chromatographed on silica gel (10 g FlashSmart column)
washeluted with ethyl acetate

Sources & evidence

ORD record: ord-a82034951d314e2ab10d9fe94cfcdb90
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863332B2

Reaction notes

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