L-Isoleucine → HCID 66739245, compound

HRID 908066Notes

Reaction equation

HRID 908066 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]>S(=O)(=O)(O)O.O.C(O)CCC.C1(C)C=CC=CC=1>[C:7]([OH:9])(=[O:8])[CH2:2][CH2:3][CH3:4].[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:5]1[CH:6]=[CH:4][CH:3]=[CH:2][CH:7]=1

Participants

6

Reactant 1

HCID 6306L-Isoleucine

Product 1

HCID 66739245HCID 66739245, compound

Reagents, catalysts & solvents 4

HCID 2631-ButanolSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 1140TolueneSolvent

Procedure

16.52 g of isoleucine was dissolved in a solution of 10 g of concentrated sulfuric acid, 20 mL water, 20 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 then cooled to room temperature and washed with saturated aqueous sodium bicarbonate to neutralize acidic impurities, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the resulting liquid distilled under vacuum to provide phenylalanine butyrate.

Workup

  1. customequipped with a condenser
  2. temperatureThe resulting solution was heated
  3. distillationcould be distilled
  4. washwashed with saturated aqueous sodium bicarbonate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. distillationthe resulting liquid distilled under vacuum

Sources & evidence

ORD record
ord-a1bbd2408c0f4794a4a62e4ad0cb1a0f
Source dataset
uspto-grants-2011_09
Patent number
US08017159B2

Reaction notes

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