Hydrochloric Acid → HCID 16225012, compound

HRID 390675Notes

Reaction equation

HRID 390675 reaction equation
[OH-].[Na+].[CH2:3]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[C:16](\[O:21][CH3:22])/[C:17]([O:19]C)=[O:18])[CH:12]=[CH:11][C:10]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:38])[C:30]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:31])[CH:24]=1)[CH3:4].O.Cl>O1CCCC1.CO>[CH2:3]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[C:16](\[O:21][CH3:22])/[C:17]([OH:19])=[O:18])[CH:12]=[CH:11][C:10]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:38])[C:30]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:31])[CH:24]=1)[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86626112HCID 86626112, compound

Product 1

HCID 16225012HCID 16225012, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

17 mg (4.2 mmol) of sodium hydroxide are added to a solution of 211 mg (0.42 mmol) of methyl (Z)-3-[2-(2-ethoxyethoxy)-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methoxyacrylate in 5 mL of tetrahydrofuran and 0.5 mL of methanol. The reaction mixture is stirred overnight at room temperature. After addition of 10 mL of water and acidification to pH 3 with 1 N hydrochloric acid, the reaction medium is extracted with ethyl acetate. The organic phases are combined, dried over sodium sulfate and evaporated, and the residue obtained is then purified by chromatography on a column of silica eluted with a 98/2 dichloromethane/methanol mixture. 160 mg (74%) of (Z)-3-[2-(2-ethoxyethoxy)-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methoxyacrylic acid are obtained in the form of white crystals. (m.p.=78.2° C.).

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customthe residue obtained
  5. customis then purified by chromatography on a column of silica
  6. washeluted with a 98/2 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-dffdd35065c241b680fb3c40a63b20a6
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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