Sodium Hydroxide → HCID 16224226, compound

HRID 390609Notes

Reaction equation

HRID 390609 reaction equation
[OH-].[Na+].[CH3:3][N:4]([C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[C:26](\[CH2:32][CH2:33][CH3:34])/[C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6]>C(O)C>[CH3:3][N:4]([C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[C:26](\[CH2:32][CH2:33][CH3:34])/[C:27]([OH:29])=[O:28])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68964090HCID 68964090, compound

Product 1

HCID 16224226HCID 16224226, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

176 mg (4.4 mmol) of sodium hydroxide are added to a solution of 192 mg (0.44 mmol) of ethyl 2-[1-[3′-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(E)-ylidene]pentanoate in 8 mL of ethanol. The reaction mixture is heated at 50° C. for 15 hours. The reaction medium is evaporated to dryness, taken up in water, acidified with 2 N 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 solid obtained is purified by chromatography on a column of silica eluted with a 50/50 heptane/ethyl acetate mixture. The solvents are evaporated off and the oil obtained is crystallized from ethyl ether, filtered and dried. 133 mg (74%) of 2-[1-[3′-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(E)-ylidene]pentanoic acid are obtained in the form of a white powder with a melting point of 118-119° C.

Workup

  1. customThe reaction medium is evaporated to dryness
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is evaporated off
  6. customthe solid obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 50/50 heptane/ethyl acetate mixture
  9. customThe solvents are evaporated off
  10. customthe oil obtained
  11. customis crystallized from ethyl ether
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-821d8ba98f004604af6823b20a0f5a6a
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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