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

HRID 330423

반응식

HRID 330423 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7ef08bdefa5e47119bc105eb466ad06b
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04895842

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