Triethylamine → N-(4-trifluoromethylphenylcarbamoyl)-L-phenylalanine benzyl ester

HRID 1088618Notes

Reaction equation

HRID 1088618 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:30])[C@H:21]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[F:38][C:39]([F:50])([F:49])[C:40]1[CH:45]=[CH:44][C:43]([N:46]=[C:47]=[O:48])=[CH:42][CH:41]=1>O1CCCC1>[CH2:12]([O:19][C:20](=[O:30])[C@H:21]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:22][C:47](=[O:48])[NH:46][C:43]1[CH:44]=[CH:45][C:40]([C:39]([F:38])([F:50])[F:49])=[CH:41][CH:42]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 12636207L-phenylalanine benzyl ester p-toluenesulfonate

Product 1

HCID 54428191N-(4-trifluoromethylphenylcarbamoyl)-L-phenylalanine benzyl esterYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of L-phenylalanine benzyl ester p-toluenesulfonic acid salt (1.71 g) and triethylamine (405 mg) in dry tetrahydrofuran (30 ml), which was cooled to 0° C., was added 4-trifluoromethylphenyl isocyanate (748 mg). The mixture was stirred at the same temperature for 30 minutes. After evaporation of the solvent, the residue was washed with 5% hydrochloric acid, saturated sodium bicarbonate solution and water successively, dried over magnesium sulfate and concentrated under reduced pressure to give N-(4-trifluoromethylphenylcarbamoyl)-L-phenylalanine benzyl ester (1.62 g) as white crystals.

Workup

  1. customAfter evaporation of the solvent
  2. washthe residue was washed with 5% hydrochloric acid, saturated sodium bicarbonate solution and water successively
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e07f584d54b421cb1172481ff142a7f
Source dataset
uspto-grants-1990_10
Patent number
US04963530

Reaction notes

Loading…