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Ethyl chloroformate → 5-tert-Butyl 1-ethyl 3-amino-4,6-dihydropyrrolo(3,4-c)pyrazole-1,5-dicarboxylate

HRID 729240
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HRID 729240 반응식
[C:1](Cl)(=[O:5])[O:2][CH2:3][CH3:4].[NH2:7][C:8]1[C:9]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][C:10]=2[NH:11][N:12]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[NH2:7][C:8]1[C:9]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][C:10]=2[N:11]([C:1]([O:2][CH2:3][CH3:4])=[O:5])[N:12]=1
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참가 물질

5

반응물 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 11333571tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate

생성물 1

HCID 69190455-tert-Butyl 1-ethyl 3-amino-4,6-dihydropyrrolo(3,4-c)pyrazole-1,5-dicarboxylate수율 72%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of ethyl chlorocarbonate (8.9 ml, 93 mmol) in tetrahydrofuran (THF, 250 ml) was slowly added to a mixture of tert-butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate (20 g, 89 mmol) and diisopropylethylamine (DIEA, 92 ml, 528 mmol) in THF (500 ml) at 0-5° C. The reaction was kept at the same temperature for two hours then allowed to reach room temperature and stirred overnight. The obtained mixture was evaporated to dryness under vacuum, and the resulting residue extracted with ethyl acetate (AcOEt) and water. The organic layer was separated, dried over sodium sulfate and evaporated to dryness. The mixture was purified by flash-chromatography (eluent: ethyl acetate/cyclohexane 4/6 to 7/3) to give 19 g of the title compound as a white solid. [M+H]+ 297

후처리

  1. customto reach room temperature
  2. customThe obtained mixture was evaporated to dryness under vacuum
  3. extractionthe resulting residue extracted with ethyl acetate (AcOEt) and water
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe mixture was purified by flash-chromatography (eluent: ethyl acetate/cyclohexane 4/6 to 7/3)

출처 및 근거

ORD 기록
ord-90596396018e4ce69a8fbcc12e13894a
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07582628B2

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