Sodium Hydroxide → HCID 22144731, compound

HRID 1824927Notes

Reaction equation

HRID 1824927 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:24])[CH2:10][C:11]1[C:19]2[O:18][CH:17]=[CH:16][C:15]=2[CH:14]=[C:13]([C:20]([O:22]C)=[O:21])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:24])[CH2:10][C:11]1[C:19]2[O:18][CH:17]=[CH:16][C:15]=2[CH:14]=[C:13]([C:20]([OH:22])=[O:21])[CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22144912HCID 22144912, compound

Product 1

HCID 22144731HCID 22144731, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.341 gm (1.02 mMol) N-tert-butoxycarbonyl 1-(5-methoxycarbonylbenzofur-7-yl)-2-aminopropane (EXAMPLE 41) and 0.204 gm (5.1 mMol) sodium hydroxide in 2 mL ethanol and 0.5 mL water was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue dissolved in water. This aqueous solution was washed with ethyl acetate and the organic phase discarded. The remaining aqueous phase was made acidic by the addition of aqueous potassium hydrogen sulfate. The aqueous phase was again extracted with ethyl acetate. This organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from a mixture of chloroform and hexane to provide 0.300 gm (92%) of the title compound as a white crystalline solid in two crops.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in water
  3. washThis aqueous solution was washed with ethyl acetate
  4. additionThe remaining aqueous phase was made acidic by the addition of aqueous potassium hydrogen sulfate
  5. extractionThe aqueous phase was again extracted with ethyl acetate
  6. dry with materialThis organic phase was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-206cd68090844a55be3adc2889af7ff6
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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