Lithium hydroxide, monohydrate → (Z)-3-[2-butoxy-3'-(1-methyl-3-phenethylureido)biphenyl-4-yl]-2-ethoxyacrylic acid

HRID 390634Notes

Reaction equation

HRID 390634 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[C:13](\[O:18][CH2:19][CH3:20])/[C:14]([O:16]C)=[O:15])[CH:9]=[CH:8][C:7]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:39])[C:28]([NH:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:29])[CH:22]=1)[CH2:2][CH2:3][CH3:4].O1CCCC1.CO.O.O.[OH-].[Li+]>C(O)(=O)C>[CH2:1]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[C:13](\[O:18][CH2:19][CH3:20])/[C:14]([OH:16])=[O:15])[CH:9]=[CH:8][C:7]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:39])[C:28]([NH:30][CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:29])[CH:22]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21892291Methanol tetrahydrofuran waterHCID 86626092methyl (Z)-3-[2-butoxy-3'-(1-methyl-3-phenethylureido)biphenyl-4-yl]-2-ethoxyacrylate

Product 1

HCID 16224620(Z)-3-[2-butoxy-3'-(1-methyl-3-phenethylureido)biphenyl-4-yl]-2-ethoxyacrylic acidYield 38.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

40 mg (0.08 mmol) of methyl (Z)-3-[2-butoxy-3′-(1-methyl-3-phenethylureido)biphenyl-4-yl]-2-ethoxyacrylate are placed in 0.5 mL of a 5/1/1 by volume mixture of tetrahydrofuran/methanol/water, 17 mg (0.4 mmol) of lithium hydroxide monohydrate are added and the reaction medium is stirred at room temperature for 18 hours. The reaction medium is acidified to pH 3 with acetic acid and then extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with an 85/15 and then 60/40 heptane/ethyl acetate mixture. 16 mg (34%) of (Z)-3-[2-butoxy-3′-(1-methyl-3-phenethylureido)biphenyl-4-yl]-2-ethoxyacrylic acid are obtained.

Workup

  1. additionare added
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with an 85/15

Sources & evidence

ORD record
ord-c19ece460f6747b5a081fc47fca2e333
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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