Hydrochloric Acid → HCID 57543173, compound

HRID 390677Notes

Reaction equation

HRID 390677 reaction equation
[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:13]=[C:12](/[CH:14]=[C:15](/[O:20][CH3:21])\[C:16]([O:18]C)=[O:17])[CH:11]=[CH:10][C:9]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]([CH3:37])[C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:30])[CH:23]=1)[CH2:4][CH2:5][CH3:6].Cl.O.O1CC[CH2:42][CH2:41]1>C(OCC)(=O)C>[CH2:3]([O:7][C:8]1[CH:13]=[C:12](/[CH:14]=[C:15](/[O:20][CH3:21])\[C:16]([OH:18])=[O:17])[CH:11]=[CH:10][C:9]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]([CH3:37])[C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:41][CH3:42])=[O:30])[CH:23]=1)[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86626115HCID 86626115, compound

Product 1

HCID 57543173HCID 57543173, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
68 °C

Procedure

1.3 mL (1.3 mmol) of aqueous 1 M sodium hydroxide solution are added to a solution of 0.33 g (0.65 mmol) of methyl (E)-3-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methoxyacrylate in 8 mL of tetrahydrofuran. The reaction mixture is stirred at 68° C. for 6 hours. After cooling, the reaction is worked up by addition of 2 mL (2 mmol) of aqueous 1 M hydrochloric acid solution and 10 mL of water and extraction with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and then dried over magnesium sulfate. The solvents are evaporated off. The residue obtained is purified by chromatography on a column of silica eluted with a 70/30 and then 50/50 heptane/ethyl acetate mixture. The product obtained is then recrystallized from isopropyl ether to give 0.25 g (90%) of (E)-3-[2-butoxy-3′-(1-methyl-3-heptylureido)biphenyl-4-yl]-2-methoxyacrylic acid in the form of a white solid with a melting point of 89° C.

Workup

  1. temperatureAfter cooling
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvents are evaporated off
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a 70/30
  8. customThe product obtained
  9. customis then recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-043dbf140b12442f9cc9b5657ed0bc3d
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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