L-Phenylalanine → HCID 15045083, compound

HRID 1089855Notes

Reaction equation

HRID 1089855 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][CH2:15][C:16](Cl)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>[CH:1]1[C:13]2[CH:12]([CH2:14][CH2:15][C:16]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 6140L-PhenylalanineHCID 15045075HCID 15045075, compound

Product 1

HCID 15045083HCID 15045083, compound

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

3-(Fluoren-9-yl)propionyl chloride (described in Example 33; without crystallization) (3.0 g, 11.7 mmol) in dioxane (40 mL) was added to a stirred solution of L-phenylalanine ((2.0 g, 11.7 mmol) in 75 mL of 10% potassium carbonate solution and 38 mL of dioxane at room temperature. The reaction mixture was stirred overnight. The dioxane was removed under reduced pressure. The residue was diluted with water (100 mL) and extracted with ethyl acetate (4×30 mL). The water solution was treated with Norit then acidified to pH 1. The precipitate was filtered off, washed with 1N HCl, water and dried. Short path chromatography (RP-18 Silica, 50% methanol/water) afforded white solid. Final purification was accomplished by washing the product with ether. The resulting yield of N-[9H-(3-fluoren-9-ylpropionyl)]-L-phenylalanine was 1.2 g 26.5%), mp 194°-195° C.

Workup

  1. customat room temperature
  2. customThe dioxane was removed under reduced pressure
  3. additionThe residue was diluted with water (100 mL)
  4. extractionextracted with ethyl acetate (4×30 mL)
  5. additionThe water solution was treated with Norit
  6. filtrationThe precipitate was filtered off
  7. washwashed with 1N HCl, water
  8. customdried
  9. customShort path chromatography (RP-18 Silica, 50% methanol/water) afforded white solid
  10. customFinal purification
  11. washby washing the product with ether

Sources & evidence

ORD record
ord-10006cb8b4b44a7c8b7974f6d52b742f
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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