Hydrochloric Acid → (Z)-3-[2-butoxy-3'-(3-heptylureido)biphenyl-4-yl]-2-methoxyacrylic acid

HRID 390694Notes

Reaction equation

HRID 390694 reaction equation
[OH-].[Li+].[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]([NH:28][C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:30])[CH:23]=1)[CH2:4][CH2:5][CH3:6].O.Cl>O1CCCC1>[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]([NH:28][C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:30])[CH:23]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 86626123methyl (Z)-3-[2-butoxy-3'-(3-heptylureido)biphenyl-4-yl]-2-methoxyacrylate

Product 1

HCID 16225217(Z)-3-[2-butoxy-3'-(3-heptylureido)biphenyl-4-yl]-2-methoxyacrylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.3 mL (1.3 mmol) of aqueous 1 N lithium hydroxide solution are added to a solution of 423 mg (0.87 mmol) of methyl (Z)-3-[2-butoxy-3′-(3-heptylureido)biphenyl-4-yl]-2-methoxyacrylate in 10 mL of tetrahydrofuran. The reaction mixture is stirred for 24 hours at room temperature. After addition of 20 mL of water and acidification with 1 N hydrochloric acid, the reaction medium is extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the residue is then recrystallized from 5 mL of acetonitrile. 348 mg (85%) of (Z)-3-[2-butoxy-3′-(3-heptylureido)biphenyl-4-yl]-2-methoxyacrylic acid are obtained in the form of a white powder. (m.p.=137° C.).

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvents are evaporated off
  5. customthe residue is then recrystallized from 5 mL of acetonitrile

Sources & evidence

ORD record
ord-1f51e236e8164d6a97372078a5bd5c83
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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