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Dimethylformamide → HCID 59571721, 화합물

HRID 2194308
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HRID 2194308 반응식
[H-].[Na+].CN(C)C=O.[CH3:8][C:9]1[O:13][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:11][C:10]=1[CH2:20][O:21][C:22]1[CH:42]=[CH:41][C:25]([CH2:26][N:27]2[C:39]3[CH:38]=[CH:37][CH:36]=[C:35]([OH:40])[C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:24][C:23]=1[O:43][CH3:44].Br[C@H:46]([CH2:52][CH3:53])[C:47]([O:49][CH2:50][CH3:51])=[O:48]>O>[CH3:44][O:43][C:23]1[CH:24]=[C:25]([CH:41]=[CH:42][C:22]=1[O:21][CH2:20][C:10]1[N:11]=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:13][C:9]=1[CH3:8])[CH2:26][N:27]1[C:39]2[CH:38]=[CH:37][CH:36]=[C:35]([O:40][C@@H:46]([CH2:52][CH3:53])[C:47]([O:49][CH2:50][CH3:51])=[O:48])[C:34]=2[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 7000062130251-07-9HCID 59571732HCID 59571732, 화합물

생성물 1

HCID 59571721HCID 59571721, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

41 mg of sodium hydride (60%) was added to N,N-dimethylformamide (2.5 mL) solution of 500 mg of 9-{4-[(5-methyl-2-phenyloxazole-4-yl)methoxy]-3-methoxybenzyl}-9H-carbazole-4-ol while being cooled in an ice bath, and stirred at room temperature for 1 hour. Thereafter, 239 mg of ethyl (R)-2-bromobutyrate was added thereto dropwise at −5° C., and was stirred for 30 minutes. Water was added to the reaction mixture, and extracted twice with ethyl acetate. The combined extract was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, the residue was purified by NH silica gel chromatography (ethyl acetate:n-hexane=1:4), and 650 mg of the subject compound was prepared. Optical purity 95% ee (HPLC).

후처리

  1. temperaturewhile being cooled in an ice bath
  2. stirringdropwise at −5° C., and was stirred for 30 minutes
  3. extractionextracted twice with ethyl acetate
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated in vacuo
  9. customthe residue was purified by NH silica gel chromatography (ethyl acetate:n-hexane=1:4), and 650 mg of the subject compound
  10. customwas prepared

출처 및 근거

ORD 기록
ord-cd99b0be457249f3b45574a6b0d4a77a
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08329913B2

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