L-Tyrosine → N-Formyl-L-tyrosine

HRID 1581909Notes

Reaction equation

HRID 1581909 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](OC(=O)C)(=[O:16])C>C(O)=O.O>[CH:14]([NH:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:16]

Participants

5

Reactant 2

HCID 6057L-TyrosineHCID 7918Acetic Anhydride

Product 1

HCID 13025455N-Formyl-L-tyrosineYield 88%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

L-Tyrosine (60 g; 0.33 mol) was dissolved in 98% formic acid (400 ml) and cooled to 10° C. Acetic anhydride, (192 ml; 1.73 mol) was added in four stages for five minutes, while at the same time maintaining a temperature of 10° C. The mixture was then stirred for 60 min at 10° C. and then kept at room temperature for 30 min. Water (192 ml) was added with stirring at 10 to 15° C. for 30 min, and then the mixture was subjected to evaporation under reduced pressure at 70° C., until a dry residue was obtained. The residual oily solid was dissolved in a minimal volume of boiling water, and then cooled to produce fine white crystals of N-formyl-L-tyrosine (60.6 g; 88%).

Workup

  1. temperaturemaintaining a temperature of 10° C
  2. waitkept at room temperature for 30 min
  3. stirringwith stirring at 10 to 15° C. for 30 min
  4. customthe mixture was subjected to evaporation under reduced pressure at 70° C., until a dry residue
  5. customwas obtained
  6. temperaturecooled

Sources & evidence

ORD record
ord-5065c6b91aec4f44ac5c01f4fe1e813a
Source dataset
uspto-grants-2004_05
Patent number
US06733986B1

Reaction notes

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