Acetyl chloride → N-acetyl-N-(9-fluorenyl)-beta-alanin ethyl ester

HRID 1729252Notes

Reaction equation

HRID 1729252 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[CH2:12]([O:14][C:15](=[O:32])[CH2:16][CH2:17][NH:18][CH:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:13]>C(Cl)Cl>[CH2:12]([O:14][C:15](=[O:32])[CH2:16][CH2:17][N:18]([C:8](=[O:10])[CH3:9])[CH:19]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=2[C:26]2[C:31]1=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:13]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14896448HCID 14896448, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.51 mg of triethylamine and 0.28 ml of acetyl chloride were added under ice-cooling to a solution of 0.77 g of N-(9-fluorenyl)-β-alanine ethyl ester in 25 ml of methylene chloride. The resultant mixture was stirred at 0° C. for 0.5 hour and, then, at room temperature for 3 hours. The reaction solution was poured into ice-cold 1N hydrochloric acid and extracted with methylene chloride. The organic layer was washed with saturated sodium bicarbonate and saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by a silica gel column chromatography (eluting solution: chloroform-methanol) to give 0.85 g of N-acetyl-N-(9-fluorenyl)-β-alanin ethyl ester.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with saturated sodium bicarbonate and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by a silica gel column chromatography (eluting solution: chloroform-methanol)

Sources & evidence

ORD record
ord-0d230d05ec934f549fab6617307721ad
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

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