L-Phenylalanine → HCID 10979494, compound

HRID 1586650Notes

Reaction equation

HRID 1586650 reaction equation
[C:1](=[O:20])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[NH2:21][C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(#N)C>C(#N)C.O.[OH-].[Na+].O>[N:7]1[CH:6]=[CH:5][C:4]([CH2:3][O:2][C:1]([NH:21][C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:20])=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 6140L-PhenylalanineHCID 6342AcetonitrileHCID 14725098HCID 14725098, compound

Product 1

HCID 10979494HCID 10979494, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

8 g of 4-pyridylmethyl 4-nitrophenyl carbonate and 4.82 g of L-phenylalanine were dissolved in 350 ml of acetonitrile/water 1:1, and about 45 ml of 2N NaOH were added to pH 10. The mixture was stirred overnight and was freed from the acetonitrile in vacuo. The aqueous solution was brought to pH 6, washed three times with diethyl ether, subsequently brought to pH 1 and concentrated to give a solid residue. This was dissolved in water and the solution was extracted intensively with ethyl acetate and then brought to pH 2 and the precipitate which had separated out was filtered off with suction. After drying, the precipitate weighed 7.3 g.

Workup

  1. additionwere added to pH 10
  2. washwashed three times with diethyl ether
  3. concentrationconcentrated
  4. customto give a solid residue
  5. extractionthe solution was extracted intensively with ethyl acetate
  6. customthe precipitate which had separated out
  7. filtrationwas filtered off with suction
  8. customAfter drying

Sources & evidence

ORD record
ord-ffff599d90f94fc1a7dfb18fda1387d2
Source dataset
uspto-grants-1993_06
Patent number
US05215968

Reaction notes

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