L-Phenylalanine → HCID 15940258, compound

HRID 1677220Notes

Reaction equation

HRID 1677220 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[C:13](Cl)(=[O:15])[CH3:14]>[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>[C:13]([NH:12][C@@H:8]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:9]([OH:11])=[O:10])(=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 6140L-PhenylalanineHCID 6367Acetyl chloride

Product 1

HCID 15940258HCID 15940258, compoundYield 123.5%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of L-diphenylalanine (100 mg, 0.4 mmol) (Peptech Corp.) in 5 mL 1N NaOH and 0.5 mL saturated Na2CO3 (resulting solution at pH 10) was added acetyl chloride (0.5 mmol) dissolved in 5 mL. Afterwards, the reaction mixture was stirred at room temperature for 2 h. The alkaline solution was extracted once with ether (10 mL) and the aqueous phase was acidified with 1N HCl. This was extracted twice with 20 mL EtOAc, and the combined organic phases were washed with 50 mL 1N HCl. The organic phase was dried over Na2SO4, filtered and evaporated to an oil, which solidifies to yields 70 mg (60%) of the desired material. This crude intermediate was used as such in the next step.

Workup

  1. dissolutiondissolved in 5 mL
  2. extractionThe alkaline solution was extracted once with ether (10 mL)
  3. extractionThis was extracted twice with 20 mL EtOAc
  4. washthe combined organic phases were washed with 50 mL 1N HCl
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to an oil, which

Sources & evidence

ORD record
ord-64224484f59a4afcb13c4b734c841db5
Source dataset
uspto-grants-2011_08
Patent number
US08008297B2

Reaction notes

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