1-Butanol → L-Tyrosine, butanoate (ester)

HRID 1640341Notes

Reaction equation

HRID 1640341 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.S(=O)(=O)(O)O.[CH2:19]([OH:23])[CH2:20][CH2:21][CH3:22]>O.C1(C)C=CC=CC=1>[C:19]([O:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C@@H:2]([C:11]([OH:13])=[O:12])[NH2:1])=[CH:9][CH:8]=1)(=[O:23])[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 6057L-Tyrosine

Product 1

HCID 66739174L-Tyrosine, butanoate (ester)

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

18.19 g of tyrosine was suspended in a solution of 9.8 g of concentrated sulfuric acid, 40 mL water, 40 mL of butanol, and 200 mL of toluene in a 500 mL round bottom flask equipped with a condenser and a Dean-Stark apparatus. The resulting solution was heated at reflux temperature until no more water could be distilled. The resulting solution was cooled in an ice bath, which caused the solution to separate into two phases. The upper phase was discarded and the lower phase, an oily syrup, was retained. The syrup was mixed with sufficient 5% aqueous sodium bicarbonate solution to neutralize acidic impurities to provide a solid that was collected by filtration and washed with cold water. The resulting solid was re-crystallized in ethyl acetate.

Workup

  1. customequipped with a condenser
  2. temperatureThe resulting solution was heated
  3. distillationcould be distilled
  4. temperatureThe resulting solution was cooled in an ice bath
  5. customto separate into two phases
  6. additionThe syrup was mixed with sufficient 5% aqueous sodium bicarbonate solution
  7. customto provide a solid
  8. filtrationthat was collected by filtration
  9. washwashed with cold water
  10. customThe resulting solid was re-crystallized in ethyl acetate

Sources & evidence

ORD record
ord-049e2599e6fa404683b37b5c733022c7
Source dataset
uspto-grants-2012_02
Patent number
US08114440B2

Reaction notes

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