Hydrochloric Acid → (-)-N-Acetylphenylalanine

HRID 267308Notes

Reaction equation

HRID 267308 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](OC(=O)C)(=[O:17])[CH3:16].Cl>O>[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:17])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide2×HCID 71567D-Phenylalanine

Product 1

HCID 101184(-)-N-Acetylphenylalanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 20.0 parts of D-phenylalanine in 121 parts of water, cooled to about 1°-2°, is added, portionwise, an aqueous 50% sodium hydroxide solution until pH 12 is reached. Then 37 parts of acetic anhydride is added, while continuously adding aqueous 50% sodium hydroxide to keep the pH at about 12 and cooling the solution to keep the temperature at between about 10° to 30°. After about 20 minutes the mixture is acidified to pH 1 with concentrated hydrochloric acid and filtered. The recovered solid is recrystallized from water to afford N-acetyl-D-phenylalanine, melting at about 170°-172°.

Workup

  1. additionis added
  2. temperaturecooling the solution
  3. customat between about 10° to 30°
  4. filtrationfiltered
  5. customThe recovered solid is recrystallized from water

Sources & evidence

ORD record
ord-3e4cb65faaae4dcc8be568c3fe4c67a0
Source dataset
uspto-grants-1976_03
Patent number
US03941831

Reaction notes

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