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Tetrahydrofuran → N-[4-(t-butyloxycarbonyl)aminomethylbenzoyl]-4-benzyloxy-L-phenylalanine cyclohexylamide

HRID 330435
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HRID 330435 반응식
C[CH:2]1[CH:7](C)[CH2:6][CH2:5][CH:4]([NH:9][C:10](=[O:45])[C@H:11]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:33][CH:32]=2)[NH:12][C:13](=[O:29])[C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:16][CH:15]=2)[CH2:3]1.O1CCCC1.C(N(CC)CC)C>CN(C)C=O>[CH:4]1([NH:9][C:10](=[O:45])[C@H:11]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:33][CH:32]=2)[NH:12][C:13](=[O:29])[C:14]2[CH:15]=[CH:16][C:17]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[CH:18][CH:19]=2)[CH2:5][CH2:6][CH2:7][CH2:2][CH2:3]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 54354000N-[4-(t-butyloxycarbonyl)aminomethylbenzoyl]-4-benzyloxy-L-phenylalanine 3,4-dimethylcyclohexylamide

생성물 1

HCID 53735669N-[4-(t-butyloxycarbonyl)aminomethylbenzoyl]-4-benzyloxy-L-phenylalanine cyclohexylamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The above compound (III) was suspended in dimethylformamide (10 ml)--tetrahydrofuran (10 ml) solution, and triethylamine (0.4 ml) and trans-4-(t-butyloxycarbonyl)aminomethylcyclohexylcarboxylic acid mixed acid anhydride were added under ice-cooling, followed by stirring for 30 minutes. Further, the reaction was carried out at room temperature for 3 hours. After a conventional post-treatment, N-[trans-4-(t-butyloxycarbonyl)aminomethylcyclohexylcarbonyl]-4-(3-cyanobenzyloxy)-L-phenylalanine 4-acetylanilide (IV) (1.31 g) was obtained. The above compound (IV) (1.31 g) was allowed to react with 4N-hydrogen chloride/dioxane solution (10 ml) for 1 hour, and the crystalline substance precipitated by addition of hexane was collected by filtration. The product was recrystallized from an ethanol-ether solution to obtain N-(trans-4-aminomethylcyclohexylcarbonyl)-4-(3-cyanobenzyloxy)-L-phenylalanine 4-acetylanilide hydrochloride (1.1 g).

후처리

  1. temperaturecooling
  2. waitFurther, the reaction was carried out at room temperature for 3 hours

출처 및 근거

ORD 기록
ord-71c231515dee4c5aa7ac871b163b8cb4
출처 데이터셋
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04895842

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