Triethylamine → N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 3-pyridylamide

HRID 330423

反応式

HRID 330423 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25](O)=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:41][C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1>O1CCCC1>[N:44]1[CH:45]=[CH:46][CH:47]=[C:42]([NH:41][C:25](=[O:26])[C@H:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:16]=2)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:43]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 10928Ethyl chloroformateHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine

生成物 1

HCID 54368616N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 3-pyridylamide収率 22.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine (I) (3.71 g) was dissolved in dry tetrahydrofuran (100 ml) and, under ice cooling, triethylamine (1.5 ml) was added thereto. After stirring for 15 minutes, ethyl chlorocarbonate (1.10 g) was added, followed by stirring for 30 minutes. To this solution was added 3-aminopyridine (0.94 g) and the reaction was carried out at room temperature for 7 hours. The solid was filtered off and the filtrate was concentrated under reduced pressure. The residue was extracted with ethyl acetate. After a conventional post-treatment, N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 3-pyridylamide (II) (1.01 g) was obtained.

後処理

  1. stirringby stirring for 30 minutes
  2. waitthe reaction was carried out at room temperature for 7 hours
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. extractionThe residue was extracted with ethyl acetate

出典と根拠

ORDレコード
ord-7ef08bdefa5e47119bc105eb466ad06b
出典データセット
uspto-grants-1990_01
特許番号
US04895842

関連ノート

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