Hydrochloric Acid → Benzoyl-L-phenylalanine

HRID 617632Notes

Reaction equation

HRID 617632 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>CCOCC>[C:15]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 97370Benzoyl-L-phenylalanineYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of phenylalanine (500 g, 3.03 mol), 2N aqueous sodium hydroxide solution (4 L) and ether (500 mL) was added dropwise benzoyl chloride (455 mL, 3.93 mol) under ice-cooling over about 55 min. The resulting mixture was stirred at room temperature for 16 h, cooled with ice and acidified with conc. hydrochloric acid to pH 2. The precipitated crystals were extracted with ethyl acetate. The obtained extracts were combined and washed with water, dried over anhydrous sodium sulfate and concentrated to ca. 2 L. Then hexane was added to the resulting suspension. The resulting precipitate was collected by filtration to give 815 g (100%) of N-benzoylphenylalanine.

Workup

  1. temperaturecooling over about 55 min
  2. temperaturecooled with ice
  3. extractionThe precipitated crystals were extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to ca. 2 L
  7. additionThen hexane was added to the resulting suspension
  8. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-0cfd9f714f174910b8dee593b032d8cc
Source dataset
uspto-grants-1999_09
Patent number
US05948785

Reaction notes

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