Hydrochloric Acid → Benzoyl-L-phenylalanine

HRID 1065542Notes

Reaction equation

HRID 1065542 reaction equation
[NH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>[OH-].[Na+]>[C:13]([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:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 994Dl-PhenylalanineHCID 7412Benzoyl chloride

Product 1

HCID 97370Benzoyl-L-phenylalanineYield 87.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 165 g of d,l-phenylalanine in 1100 ml of 1 N sodium hydroxide was added simultaneously 1000 ml of 1 N sodium hydroxide and 146 g of benzoyl chloride over a period of 1 hr with maintenance of the temperature at 2°-5° C. After 3 hr at 5°-10° C., the solution was acidified to pH4 with 5 N hydrochloric acid. The precipitate was collected, washed with water and acetone and dried to leave 234.5 g (87%) of N-benzoyl phenylalanine, mp 185°-188° C. The material was mixed with 2000 ml of acetic anhydride and heated at 95°-100° for 45 minutes. The solvent was removed in vacuo to afford 222 g (100%) of the azlactone, m.p. 60° C.

Workup

  1. customThe precipitate was collected
  2. washwashed with water and acetone
  3. customdried

Sources & evidence

ORD record
ord-2d66fdab78964f229d83993ee9834800
Source dataset
uspto-grants-1982_05
Patent number
US04329473

Reaction notes

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