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Dimethyl Sulfoxide → HCID 67193954, 화합물

HRID 1951664
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HRID 1951664 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:22])[C:9](=[O:21])[C:10]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)([CH3:12])[CH3:11])=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[CH:3]=1.[OH:30][C@H:31]1[CH2:35][NH:34][C@H:33]([CH2:36][OH:37])[CH2:32]1.CS(C)=O>C([O-])(O)=O.[Na+]>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:4]1[CH:3]=[C:2]([N:34]2[CH2:35][C@H:31]([OH:30])[CH2:32][C@H:33]2[CH2:36][OH:37])[N:7]=[CH:6][C:5]=1[N:8]([CH3:22])[C:9](=[O:21])[C:10]([C:13]1[CH:14]=[C:15]([Cl:20])[CH:16]=[C:17]([Cl:19])[CH:18]=1)([CH3:12])[CH3:11]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 15817396(3R,5S)-5-(Hydroxymethyl)pyrrolidin-3-OLHCID 86597667HCID 86597667, 화합물

생성물 1

HCID 67193954HCID 67193954, 화합물수율 31%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

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온도
13 °C

실험 절차

To a solution of 0.15 g (0.32 mmol) N-[6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3,5-dichloro-phenyl)-N-methyl-isobutyramide and 0.25 g (2.13 mmol) (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine in 2 ml dimethyl sulfoxide 0.2 g (1.55 mmol) Na2CO3 was added and the solution was stirred at 13° C. for 9 h After cooling to ambient temperature, the solution was poured into 20 ml 0.5 N NaHCO3-solution and extracted three times with 30 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash-chromatography (SiO2, CH2Cl2/ethyl acetate 1:2) to give 0.05 g (31%) of the title compound as a white foam. MS m/e (%): 548.3 (M+H+, 100).

후처리

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted three times with 30 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash-chromatography (SiO2, CH2Cl2/ethyl acetate 1:2)

출처 및 근거

ORD 기록
ord-3f96e47df24545728113255305571b08
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08404708B2

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