Sodium Hydroxide → HCID 59301172, compound

HRID 2235829Notes

Reaction equation

HRID 2235829 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([OH:29])=[O:28])[CH:22]=2)[C:9]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:7])C>C(O)CO>[C:27]([C:23]1[CH:22]=[C:21]([N:10]2[C:11]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:12][C:8]([C:6]([OH:7])=[O:5])=[C:9]2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)([OH:29])=[O:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24797742HCID 24797742, compound

Product 1

HCID 59301172HCID 59301172, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Solid NaOH (90 mg; 2.3 mmol) was added to a soln of 1-(3-carboxy-phenyl)-5-phenethyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester (157 mg; 0.357 mmol) in ethylene glycol (2.0 mL) at 160° C. After 1.6 h, the r×n was cooled then quenched with 1 M HCl (5 mL). The product was extracted into EtOAc (3×3 mL) and this soln was washed with water (3×3 mL) and satd NaCl (2×3 mL). After drying over MgSO4, filtration through silica with an EtOAc wash and concd, crude product was obtained. LC-MS 412 ([M+H]+).

Workup

  1. temperaturethe r×n was cooled
  2. customthen quenched with 1 M HCl (5 mL)
  3. extractionThe product was extracted into EtOAc (3×3 mL)
  4. washthis soln was washed with water (3×3 mL) and satd NaCl (2×3 mL)
  5. dry with materialAfter drying over MgSO4, filtration through silica with an EtOAc
  6. washwash
  7. customconcd, crude product was obtained

Sources & evidence

ORD record
ord-c6420c46055b48e0807488e28d650e8e
Source dataset
uspto-grants-2010_05
Patent number
US07714022B2

Reaction notes

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