Diethyl p-aminobenzylphosphonate → N-(4-diethylphosphonomethylphenyl)-4-(5-phenyl-4-isoxazolyl)butaneamide

HRID 1794387

반응식

HRID 1794387 반응식
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.[C:17]1([C:23]2[O:27][N:26]=[CH:25][C:24]=2[CH2:28][CH2:29][CH2:30][C:31](O)=[O:32])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[CH2:12]([O:11][P:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:31](=[O:32])[CH2:30][CH2:29][CH2:28][C:24]2[CH:25]=[N:26][O:27][C:23]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:16][CH:15]=1)([O:8][CH2:9][CH3:10])=[O:14])[CH3:13]

참가 물질

7

반응물 4

HCID 88358Diethyl p-aminobenzylphosphonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 222210974-(5-Phenyl-4-isoxazolyl)butanoic acid

생성물 1

HCID 22221010N-(4-diethylphosphonomethylphenyl)-4-(5-phenyl-4-isoxazolyl)butaneamide수율 94%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of diethyl 4-aminobenzylphosphonate (1.74 g), 4-(5-phenyl-4-isoxazolyl)butanoic acid (1.38 g), 1-hydroxy-1H-1,2,3-benzotriazole hydrate (1.08 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.38 g) and N,N-dimethylformamide (20 ml) was stirred at room temperature overnight. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate and then saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and N-(4-diethylphosphonomethylphenyl)-4-(5-phenyl-4-isoxazolyl)butaneamide (2.56 g, yield 94%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 128–129° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate
  3. dry with materialsaturated brine, dried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dd92d1ef88424fa58437d06829105446
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022725B2

연결된 노트

불러오는 중…