L-Phenylalanine → HCID 18649853, compound

HRID 2082324Notes

Reaction equation

HRID 2082324 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[P:20]([O-:37])([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O.C(O)C.C(Cl)(Cl)(Cl)Cl>[CH2:22]([O:21][P:20]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:37])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 3

HCID 6140L-PhenylalanineHCID 8471TriethylamineHCID 21904359Dibenzylphosphite

Product 1

HCID 18649853HCID 18649853, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 8.2 g of L-phenylalanine and 25 ml of triethylamine in 15 ml of water and 10 ml of ethanol under argon is chilled to 0° C. To this stirred solution is added dropwise 13.1 g of dibenzyl phosphite in 20 ml of carbon tetrachloride. After the addition, the mixture is stirred at room temperature for 3 hours and the mixture is concentrated under vacuum, diluted with ethyl acetate (100 ml), cooled to 0° C. and 50 ml of 3N hydrochloric acid added dropwise. The organic layer is separated and the aqueous layer extracted twice with 100 ml of ethyl acetate. The organic layer and extracts are combined, dried (Na2SO4) and the solvent removed. The residue is dried under vacuum to give 20.7 g of a yellow gum.

Workup

  1. additionAfter the addition
  2. concentrationthe mixture is concentrated under vacuum
  3. additiondiluted with ethyl acetate (100 ml)
  4. temperaturecooled to 0° C.
  5. addition50 ml of 3N hydrochloric acid added dropwise
  6. customThe organic layer is separated
  7. extractionthe aqueous layer extracted twice with 100 ml of ethyl acetate
  8. dry with materialdried (Na2SO4)
  9. customthe solvent removed
  10. customThe residue is dried under vacuum

Sources & evidence

ORD record
ord-860592d4dcc243939ada6c7830742666
Source dataset
uspto-grants-1993_02
Patent number
US05189023

Reaction notes

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