Triethylamine → N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine 4-pyridylamide

HRID 2351825Notes

Reaction equation

HRID 2351825 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:24](O)=[O:25])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:40][C:41]1[CH:46]=[CH:45][N:44]=[C:43](Cl)[CH:42]=1>O1CCCC1>[N:44]1[CH:45]=[CH:46][C:41]([NH:40][C:24](=[O:25])[CH:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 844322-Chloropyridin-4-amineHCID 148371622-((tert-Butoxycarbonyl)amino)-3-(3-phenoxyphenyl)propanoic acid

Product 1

HCID 54231549N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine 4-pyridylamideYield 11.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine (4.40 g) was dissolved in dry tetrahydrofuran (100 ml) and triethylamine (1.80 ml) was added under ice-cooling, followed by stirring for 15 minutes. To this solution was added ethyl chlorocarbonate (1.44 g) and the mixture was stirred for 30 minutes. After adding 4-amino-2-chloropyridine (1.54 g), the reaction was carried out at room temperature for 10 hours. Thereafter, the solid was filtered off and the filtrate was concentrated under a reduced pressure. The residue was extracted with ethyl acetate. The extract was purified with a column chromatography (hexane/ethyl acetate=3/1) to obtain N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine 4-(2-chloro)pyridylamide (I) (0.60 g), which was confirmed by the following NMR analysis, in the form of a white powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes
  3. waitthe reaction was carried out at room temperature for 10 hours
  4. filtrationThereafter, the solid was filtered off
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. extractionThe residue was extracted with ethyl acetate
  7. customThe extract was purified with a column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-779bc097ce03442985ad099aa1df2136
Source dataset
uspto-grants-1989_10
Patent number
US04873253

Reaction notes

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