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Di-tert-butyl dicarbonate → Ethyl 5-(2-{[(tert-butoxycarbonyl)-amino]methyl}phenyl)thiophene-2-carboxylate

HRID 1712936
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HRID 1712936 반응식
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:10]=1)#[N:2].[O:19](C(OC(C)(C)C)=O)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O>CO.[Ni]>[C:23]([O:22][C:20]([NH:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:10]=1)=[O:19])([CH3:26])([CH3:25])[CH3:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 90495Di-tert-butyl dicarbonateHCID 68705066Ethyl 5-(2-cyanophenyl)thiophene-2-carboxylate

생성물 1

HCID 59463267Ethyl 5-(2-{[(tert-butoxycarbonyl)-amino]methyl}phenyl)thiophene-2-carboxylate수율 86.1%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

To a slurry of ethyl 5-(2-cyanophenyl)thiophene-2-carboxylate (1.09 gm 4.24 mmol) in MeOH (8 mL) was added (BOC)2O (1.11 g, 5.08 mmol) and Raney Nickel (3.6 mL). The reaction mixture was allowed to stir at rt under an atmosphere of hydrogen overnight and then filtered through celite. The filtrate was concentrated and the residue was purified by column chromatography to give ethyl 5-(2-{[(tert-butoxycarbonyl)-amino]methyl}phenyl)thiophene-2-carboxylate (1.32 g, 86%).

후처리

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-b4400d6d0b4c41419b9e81927282f9f3
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795249B2

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