Sodium Hydroxide → HCID 57435157, compound

HRID 1366962Notes

Reaction equation

HRID 1366962 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[NH:9][C:10]([CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:12]=1)=[O:7])C>CO>[C:16]1([CH2:15][CH2:14][CH2:13][C:10]2[NH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:12][CH:11]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57435158HCID 57435158, compound

Product 1

HCID 57435157HCID 57435157, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 1.22 mmol) was added to a stirring, room temperature solution of 5-(3-phenylpropyl)-1H-pyrrole-2-carboxylic acid ethyl ester (85) (0.0629 g, 0.244 mmol) in MeOH (0.61 mL, 0.4 M) under N2. The reaction was heated to reflux until the reaction was judged complete by HPLC. The product was concentrated and then 2 mL of diethyl ether and 2 mL of H2O were added. The organic layer was removed and discarded, then 2 mL of diethyl ether was added, and 10% aq. HCl was added dropwise until the pH=2. The diethyl ether later was removed, and the aqueous was extracted with another portion of diethyl ether. The combined organics were dried, and concentrated to provide the desired product. (Note: An undesired impurity has a retention time of 10.85 min by HPLC. HPLC: 9.91 min.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux until the reaction
  3. concentrationThe product was concentrated
  4. addition2 mL of diethyl ether and 2 mL of H2O were added
  5. customThe organic layer was removed
  6. addition2 mL of diethyl ether was added
  7. addition10% aq. HCl was added dropwise until the pH=2
  8. customThe diethyl ether later was removed
  9. extractionthe aqueous was extracted with another portion of diethyl ether
  10. customThe combined organics were dried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-05942be2f2be41de8432b06489f38fe7
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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