Hydrochloric Acid → N,O-Dibenzoyltyrosine

HRID 543232Notes

Reaction equation

HRID 543232 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>[OH-].[Na+]>[C:14]([NH:1][CH:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)[C:11]([OH:13])=[O:12])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6057L-TyrosineHCID 7412Benzoyl chloride

Product 1

HCID 20205917N,O-Dibenzoyltyrosine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Tyrosine (5.0 g) was dissolved in 30 ml of 2N sodium hydroxide at 0° C. To this solution, 7 ml of benzoyl chloride was added portion-wise. The pH of the solution was constantly monitored and kept at approximately 10. After approximately 4 hours with constant pH the solution was acidified to pH 3.0 with concentrated hydrochloric acid, yielding a precipitate which was left at 0° C. for 2 hours. The precipitate was filtered, boiled over carbon tetrachloride and recrystallized from ethanol-water (1:1).

Workup

  1. customyielding a precipitate which
  2. filtrationThe precipitate was filtered
  3. customrecrystallized from ethanol-water (1:1)

Sources & evidence

ORD record
ord-f0d609cd39594271a1a848ac11d3c10a
Source dataset
uspto-grants-1987_04
Patent number
US04661510

Reaction notes

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