Benzyl chloroformate → methyl 3-(benzyloxycarbonyl)-5-tert-butyl-1H-pyrrole-2-carboxylate

HRID 18926

반응식

HRID 18926 반응식
N[C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].[H-].[Na+].[C:17](Cl)(=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.C(OCC)(=O)C>[CH2:19]([O:18][C:17]([C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12])=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 18322367methyl 3-amino-5-(tert-butyl)-1H-pyrrole-2-carboxylate

생성물 1

HCID 68682038methyl 3-(benzyloxycarbonyl)-5-tert-butyl-1H-pyrrole-2-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of the previously prepared methyl 3-amino-5-tert-butyl-1H-pyrrole-2-carboxylate (0.400 g, 2.0 mmol) and NaH (60% w/w, 0.760 g, 4.5 mmol) in THF (4 mL) was stirred at room temperature for 30 min. To the resulting mixture was added benzyl carbonochloridate drop wise and stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The crude product was recrystallized from dichloromethane:hexane to afford the desired methyl 3-(benzyloxycarbonyl)-5-tert-butyl-1H-pyrrole-2-carboxylate (0.560 g) as a white solid.

후처리

  1. stirringstirred at room temperature overnight
  2. washwashed with saturated sodium bicarbonate solution
  3. customThe crude product was recrystallized from dichloromethane

출처 및 근거

ORD 기록
ord-15201a1c4ea34fa8bc1c4db79bf5c082
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741479B2

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