Citric Acid → HCID 58508897, compound

HRID 454676Notes

Reaction equation

HRID 454676 reaction equation
CO.[OH-].[Na+].C([O:8][C:9]1[CH:42]=[CH:41][C:40]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:39][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[N:28](C(OC(C)(C)C)=O)[CH:29]=[CH:30][CH:31]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18]C(C)(C)C)=[O:17])=[O:12])(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C.O.O1CCOCC1>[OH:8][C:9]1[CH:42]=[CH:41][C:40]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:39][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[NH:28][CH:29]=[CH:30][CH:31]=2)[CH:24]=[CH:23][C:15]=1[C:16]([OH:18])=[O:17])=[O:12]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 66990165HCID 66990165, compound

Product 1

HCID 58508897HCID 58508897, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

Methanol (2.0 mL) and a 4 mol/L aqueous solution of sodium hydroxide (0.19 mL) were added to a dioxane (2.0 mL) solution of the obtained tert-butyl 2-(2-acetoxy-5-(piperidin-1-yl)benzamido)-4-(1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl)benzoate, followed by stirring at 55° C. for 1 hour. The reaction mixture was cooled to room temperature, and then a 4 mol/L aqueous solution of sodium hydroxide (0.077 mL) was added thereto, followed by stirring at 60° C. for 2 hours. The reaction mixture was cooled to room temperature and then adjusted to a pH of 7.8 with a 10% aqueous solution of citric acid, and water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-91% chloroform/methanol] to obtain 8 mg of 2-(2-hydroxy-5-(piperidin-1-yl)benzamido)-4-(1H-pyrrol-2-yl)benzoic acid as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring at 60° C. for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additionwere added
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-91% chloroform/methanol]

Sources & evidence

ORD record
ord-2fcccf454f8f4e73ab34ce6a354527eb
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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