1-Hydroxybenzotriazole → Tert-butyl (trans-2-{4-[({3-[(phenylcarbonyl)amino]phenyl}carbonyl)amino]phenyl}-cyclopropyl)carbamate

HRID 922511노트

반응식

HRID 922511 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[C:19]1([C:25]([NH:27][C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)[C:31](O)=[O:32])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>C(#N)C.C(OCC)(=O)C.O.C(N(CC)CC)C>[C:14]([O:13][C:12](=[O:18])[NH:11][C@@H:9]1[CH2:10][C@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:31]([C:30]2[CH:34]=[CH:35][CH:36]=[C:28]([NH:27][C:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:26])[CH:29]=2)=[O:32])=[CH:3][CH:4]=1)([CH3:15])([CH3:17])[CH3:16]

참가 물질

9

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 2566173-(benzoylamino)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86673140rac-tert-butyl N-[(1R,2S)-2-(4-aminophenyl)cyclopropyl]carbamate

생성물 1

HCID 131734968Tert-butyl (trans-2-{4-[({3-[(phenylcarbonyl)amino]phenyl}carbonyl)amino]phenyl}-cyclopropyl)carbamate수율 96.2%

시약·촉매·용매 4

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of tert-butyl [trans-2-(4-aminophenyl)cyclopropyl]carbamate (124 mg) described in a document (J. Am. Chem. Soc., 2010, 132, 6827.) in acetonitrile (4 mL) were added 3-[(phenylcarbonyl)amino]benzoic acid (100 mg), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (95 mg), 1-hydroxybenzotriazole (67.2 mg) and triethylamine (69 μL). The mixture was stirred at room temperature overnight and water was added. Ethyl acetate was added to the mixture, and the resulting solid was collected by filtration to give the title compound (188 mg).

후처리

  1. filtrationthe resulting solid was collected by filtration

출처 및 근거

ORD 기록
ord-5c493d5eb41a48f49becf7576099a802
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278931B2

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