Sodium Hydroxide → N-acetyl-N-(9-fluorenyl)-beta-alanine

HRID 1729253Notes

Reaction equation

HRID 1729253 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:26])[CH2:7][CH2:8][N:9]([C:23](=[O:25])[CH3:24])[CH:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)C>C(O)C.O>[C:23]([N:9]([CH:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[C:17]2[C:22]1=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:7][C:6]([OH:26])=[O:5])(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19011663N-acetyl-N-(9-fluorenyl)-beta-alanin ethyl ester

Product 1

HCID 19011676N-acetyl-N-(9-fluorenyl)-beta-alanineYield 42.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.6 ml of 1N sodium hydroxide was added dropwise to a solution of 435 mg of N-acetyl-N-(9-fluorenyl)-β-alanine ethyl ester in 25 ml of ethanol under ice-cooling. After stirring for 4.5 hours, the reaction solution was condensed. The residue was dissolved in water and, then, washed with ether. The pH value of the water layer was adjusted to 3 to 4 with 5% hydrochloric acid. The precipitate formed was separated by filtration, washed with ice-cold water, and recrystallized from a mixture of ethyl acetate and methanol to give 168 mg of N-acetyl-N-(9-fluorenyl)-β-alanine.

Workup

  1. temperaturecooling
  2. customcondensed
  3. washwashed with ether
  4. customThe precipitate formed
  5. customwas separated by filtration
  6. washwashed with ice-cold water
  7. customrecrystallized from a mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-31db247c8daf4684b8cf6ee1ae1fdec5
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

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