Benzaldehyde → HCID 10068794, compound

HRID 373652Notes

Reaction equation

HRID 373652 reaction equation
[C:1]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC(Cl)(Cl)C>[CH2:4]([O:3][C:1]([N:11]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:22])[O:21][C@H:23]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 70878Benzyloxycarbonyl-L-phenylalanine

Product 1

HCID 10068794HCID 10068794, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 62781,1,1-TrichloroethaneSolvent

Procedure

Following the procedure of Karady, Tett. Lett., 1984, 25:4337. N-Cbz-L-phenylalanine (25 g, 83.5 mmol), benzaldehyde (18 g, 170 mmol), and p-toluenesulfonic acid (11.2 g, 58 mmol) were suspended in 1,1,1-trichloroethane (300 ml). The solution was refluxed for 18 hr and the water was removed by azeotropic distillation using a Dean-Stark trap for liquids heavier than water. After cooling, the reaction was washed with saturated aqueous NaHCO3 (3×50 ml), water (1×50 ml), dried over sodium sulfate and concentrated in vacuo to produce an orange oil. After about 1 h a solid crystallized from the oil and it was collected by vacuum filtration. The orange solid was recrystallized from ethyl acetate/hexane to produce colorless crystals (4.0 g, 12%); mp 120°-122° C. MS (CI): 405 (M+NH4)+, 388 (M+H)+.

Workup

  1. temperatureThe solution was refluxed for 18 hr
  2. customthe water was removed by azeotropic distillation
  3. temperatureAfter cooling
  4. washthe reaction was washed with saturated aqueous NaHCO3 (3×50 ml), water (1×50 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto produce an orange oil
  8. customAfter about 1 h a solid crystallized from the oil and it
  9. filtrationwas collected by vacuum filtration
  10. customThe orange solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8c7fd92da753449bb6f2d803375c5cd1
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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