Sodium Hydroxide → N-(9-fluorenylcarbonyl)glycine

HRID 1729248Notes

Reaction equation

HRID 1729248 reaction equation
[OH-].[Na+].[CH:3]1[C:15]2[CH:14]([C:16]([NH:18][CH2:19][C:20]([O:22]C)=[O:21])=[O:17])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1>C(O)C>[CH:12]1[C:13]2[CH:14]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])[C:15]3[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19011672methyl N-(9-fluorenylcarbonyl)glycinate

Product 1

HCID 19011682N-(9-fluorenylcarbonyl)glycineYield 54.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.2 ml of 1N sodium hydroxide was added dropwise under ice-cooling to a solution of 900 mg of methyl N-(9-fluorenylcarbonyl)glycinate in 55 ml of ethanol. The resultant mixture was stirred at room temperature for 1.5 hours. The residue obtained by concentrating the reaction mixture was dissolved in 0.5N sodium hydroxide, and washed with an ether. Under ice-cooling, the pH value of the aqueous layer was adjusted to 3 to 4 with 5% hydrochloric acid, and the precipitate formed was separated by filtration. The precipitate thus separated was washed with water and, then, recrystallized from a mixture of ethanol and ether to give 463 mg of N-(9-fluorenylcarbonyl)glycine as white needles.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture
  3. dissolutionwas dissolved in 0.5N sodium hydroxide
  4. washwashed with an ether
  5. temperatureUnder ice-cooling
  6. customthe precipitate formed
  7. customwas separated by filtration
  8. customThe precipitate thus separated
  9. washwas washed with water
  10. customrecrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-04d307cc84ba49ccb621f30fd810c85d
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

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