Hydrogen Peroxide → N-{4'-[(1R,2S)-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-ethoxy-1-hydroxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide

HRID 584909노트

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HRID 584909 반응식
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[CH2:15][O:16][CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)S(O)(=O)=O.C(BCCCC)CCC.[CH:37]([C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][N:52]([CH3:61])[C:53](=[O:60])[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH:46]=2)=[CH:41][CH:40]=1)=[O:38].OO>ClCCl.CO.O>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[C@@H:15]([O:16][CH2:17][CH3:18])[C@@H:37]([C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][N:52]([CH3:61])[C:53](=[O:60])[C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[CH:46]=2)=[CH:41][CH:40]=1)[OH:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 784Hydrogen PeroxideHCID 10825429(S)-4-Benzyl-3-(ethoxyacetyl)oxazolidin-2-oneHCID 22341491N-(4'-formylbiphenyl-3-ylmethyl)-N-methylbenzamideHCID 178440534HCID 178440534, 화합물

생성물 1

HCID 69693998N-{4'-[(1R,2S)-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-ethoxy-1-hydroxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide수율 48%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

1.8 g (6.7 mmol) of (S)-4-benzyl-3-(2-ethoxy-ethanoyl) oxazolidin-2-one amd 15 ml of dichloromethane are introduced into a three-necked flask under argon. 7.3 ml (8 mmol) of dibutylborane trifluoromethane-sulfonate and 1.3 ml (8 mmol) of diisopropylethylamineare successively added dropwise at 0° C., and the mixture is stirred for one hour. At −78° C., a solution of 2 g (6 mmol) of N-(4′-formylbiphenyl-3-ylmethyl)-N-methylbenzamide (prepared in Example 1(e)) in 25 ml of dichloromethane is added and the mixture is stirred for one hour. The mixture is allowed to warm to 0° C. and is treated with a pH 7 buffer solution (16 ml) in 45 ml of methanol and then with aqueous hydrogen peroxide solution (16 ml) in 45 ml of methanol and stirred for one hour at 0° C. The reaction medium is poured into water and extracted with dichloromethane, and the organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (60/40). 1.7 g (48%) of N-{4′-[(1R,2S)-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-ethoxy-1-hydroxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide are obtained.

후처리

  1. stirringthe mixture is stirred for one hour
  2. extractionextracted with dichloromethane
  3. customthe organic phase is separated out
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (60/40)

출처 및 근거

ORD 기록
ord-1f721bcc9e064ad2b69ad87fe0b2dff0
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927228B2

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