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Ammonium Acetate → HCID 53701042, 화합물

HRID 1358484
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HRID 1358484 반응식
[Si]([O:8][CH2:9][C@H:10]([N:22]1[CH:26]=[C:25]([C:27]([NH2:29])=[O:28])[N:24]=[CH:23]1)[CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C([O-])(C)=O.[NH4+]>C1COCC1>[OH:8][CH2:9][C@H:10]([N:22]1[CH:26]=[C:25]([C:27]([NH2:29])=[O:28])[N:24]=[CH:23]1)[CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 517165Ammonium AcetateHCID 2724141Tetrabutylammonium FluorideHCID 53879351HCID 53879351, 화합물

생성물 1

HCID 53701042HCID 53701042, 화합물수율 64.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To an ice cooled solution of 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(1-indolyl)-2-butyl]imidazole-4-carboxamide (176.3 mg, 0.427 mmol) in THF (5 ml) was added dropwise 1.0 M Bu4NF in THF (641 ml). After the addition was completed, the reaction mixture was stirred at ice-bath temperature for 30 minutes. 25% AcONH4 (4 ml) was added, and the resulting mixture was stirred for several minutes and then extracted with ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel (6 g) column chromatography eluting with chloroform/methanol. (10:1) to give 1-[(R)-1-hydroxy-4-(1-indolyl)-2-butyl]imidazole-4-carboxamide (81.7 mg, 64.1%) as a white solid.

후처리

  1. additionAfter the addition
  2. stirringthe resulting mixture was stirred for several minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel (6 g) column chromatography
  8. washeluting with chloroform/methanol

출처 및 근거

ORD 기록
ord-3a5f9d3589cd4ef193f686661d09fff0
출처 데이터셋
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06596738B1

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