Benzaldehyde → HCID 16394648, compound

HRID 1036639Notes

Reaction equation

HRID 1036639 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+]>C1C=CC=CC=1.FC(F)(F)C(O)=O.O>[C:18]1([CH:17]2[C:8]3[NH:9][C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:7]=3[CH2:6][C@@H:4]([C:3]([O:2][CH3:1])=[O:16])[NH:5]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 77980L-Tryptophan, methyl ester

Product 1

HCID 16394648HCID 16394648, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

To the solution of 0.06 mol of L-tryptophan methyl ester and 0.05 mol of benzaldehyde in 150 ml of benzene, 0.5 ml of trifluoroacetic acid and 2 g of molecular sieves (4 Å) were added. The reaction mixture was refluxed for 1 hour, and then 0.138 mol (3 equiv.) of trifluoroacetic acid was added and the mixture was further refluxed for 3 hours. The reaction mixture was cooled down to room temperature and diluted with water and basified with 30% solution of NaOH. The organic layer was separated, dried over MgSO4 and the solvent was removed in vacuo. The residue was washed with diethyl ether, and the precipitate thus formed was filtered off to give the required product (80% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. temperaturethe mixture was further refluxed for 3 hours
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed in vacuo
  6. washThe residue was washed with diethyl ether
  7. customthe precipitate thus formed
  8. filtrationwas filtered off

Sources & evidence

ORD record
ord-f4dc45e505e64bc6accbd8777ea360b8
Source dataset
uspto-grants-2013_10
Patent number
US08546421B1

Reaction notes

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