Hydrochloric Acid → 3-[(3-Carboxycyclohexyl)carbamoyl]-4-{3-[4-(4-phenoxybutoxy)phenyl]propoxy}benzoic acid

HRID 1782774Notes

Reaction equation

HRID 1782774 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([NH:11][C:12]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[O:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:30][CH:29]=2)[C:17]([O:19]C)=[O:18])=[O:13])[CH2:6]1)=[O:4].[OH-].[Na+].Cl>O1CCCC1.CO>[C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([NH:11][C:12]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[O:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:30][CH:29]=2)[C:17]([OH:19])=[O:18])=[O:13])[CH2:6]1)([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57589066HCID 57589066, compound

Product 1

HCID 533940343-[(3-Carboxycyclohexyl)carbamoyl]-4-{3-[4-(4-phenoxybutoxy)phenyl]propoxy}benzoic acidYield 96.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 638 mg of methyl 3-({[3-(methoxycarbonyl)cyclohexyl]-amino}carbonyl)-4-{3-[4-(4-phenoxybutoxy)phenyl]propoxy}benzoate (racemate B) in 4 ml of tetrahydrofuran (THF) and 4 ml of methanol is mixed with 4 ml of 2 molar sodium hydroxide solution and heated at 60° C. for one hour. The pH is then adjusted to a value of 3-4 with 2 molar hydrochloric acid, and the mixture is extracted with ethyl acetate. The organic extract is washed with saturated sodium chloride solution and dried over anhydrous sodium sulphate. Filtration and evaporation result in a crude product which is purified by recrystallization from diethyl ether. 589 mg of product are isolated.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. extractionThe organic extract
  3. washis washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationFiltration and evaporation
  6. customresult in a crude product which
  7. customis purified by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-14a7fad44c494ab0905b28a98cfe47e0
Source dataset
uspto-grants-2009_03
Patent number
US07498460B2

Reaction notes

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