Acetic Acid → HCID 11494981, compound

HRID 1673540Notes

Reaction equation

HRID 1673540 reaction equation
C(O)(=O)C.CO[CH:7]1[CH2:11][CH2:10][CH:9](OC)O1.[NH2:14][C:15]1[CH:39]=[CH:38][C:18]([C:19]([NH:21][C:22]2[CH:30]=[C:29]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:28]=[CH:27][C:23]=2[C:24]([OH:26])=[O:25])=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[O:31]([C:29]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[C:22]([NH:21][C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([N:14]3[CH:7]=[CH:11][CH:10]=[CH:9]3)=[CH:39][CH:38]=2)[CH:30]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 57879299HCID 57879299, compound

Product 1

HCID 11494981HCID 11494981, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

0.25 mL of acetic acid and 4.1 μL of 2,5-dimethoxytetrahydrofuran were added sequentially to 10 mg of 2-(4-aminobenzamido)-4-phenoxybenzoic acid at room temperature and stirred at 90° C. for 5 minutes. After the reaction mixture was cooled so room temperature, ethyl acetate and a saturated sodium hydrogen carbonate aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified wish silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; ethyl acetate] to obtain 3.8 mg of 4-phenoxy-2-(4-(1H-pyrrol-1-yl)benzamido)benzoic acid a brown solid.

Workup

  1. temperatureAfter the reaction mixture was cooled so room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with a saturated sodium chloride aqueous solution
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified

Sources & evidence

ORD record
ord-1c2f0a7ec156473b8e64802645a9dc26
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

Loading…