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Water → HCID 59410204, 화합물

HRID 391758
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HRID 391758 반응식
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([N:24]4[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[C:25]4=[O:31])=[C:19]([CH3:32])[CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1.Br[CH2:34][CH2:35][Cl:36].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN1CCCC1=O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([N:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:34][CH2:35][Cl:36])[C:25]4=[O:31])=[C:19]([CH3:32])[CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1
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6

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HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 594101745-Chloro-N-({(5S)-3-[4-(3-hydroxy-2-oxopyridin-1(2H)-yl)-3,5-dimethylphenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide

생성물 1

HCID 59410204HCID 59410204, 화합물

시약·촉매·용매 1

HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
60 °C

실험 절차

900 mg (1.89 mmol) of the compound from Example 72A and 1.36 g (9.49 mmol) of 1-bromo-2-chloroethane are dissolved in 30 ml of 1-methyl-2-pyrrolidone. 1.55 g (4.75 mmol) of caesium carbonate are added to the solution, and the mixture is stirred at 60° C. for 15 hours. Water is then added, and, after phase separation, the aqueous phase is extracted three times with tert-butyl methyl ether and three times with dichloromethane. The combined organic phases are washed successively with 1N aqueous sodium hydroxide solution and saturated sodium chloride solution and then dried over sodium sulphate. The drying agent is filtered off and the solvent is removed completely on a rotary evaporator. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:5). This gives 464 mg (45% of theory, purity according to LC-MS 74%) of the desired product.

후처리

  1. customafter phase separation
  2. extractionthe aqueous phase is extracted three times with tert-butyl methyl ether and three times with dichloromethane
  3. washThe combined organic phases are washed successively with 1N aqueous sodium hydroxide solution and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationThe drying agent is filtered off
  6. customthe solvent is removed completely on a rotary evaporator
  7. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:5)

출처 및 근거

ORD 기록
ord-65496adad7a44ce789cc0a71e9ad937c
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08383822B2

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