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

HRID 2351825ノート

反応式

HRID 2351825 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-779bc097ce03442985ad099aa1df2136
出典データセット
uspto-grants-1989_10
特許番号
US04873253

反応ノート

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