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Cesium carbonate → (S)-di-tert-butyl (3-(2-fluoro-4-(5-(4-(5-fluoropyridin-2-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1H-1,2,4-triazol-1-yl)methyl phosphate

HRID 539126
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HRID 539126 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:14]=[N:15][N:16]3[CH:21]=[CH:20][C:19]([N:22]4[C@@H:26]([C:27]5[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=5)[CH2:25][O:24][C:23]4=[O:34])=[N:18][C:17]=23)[CH:5]=[CH:6][C:7]=1[C:8]1[N:12]=[CH:11][NH:10][N:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[P:41]([O:53][CH2:54]Cl)([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>CN(C=O)C.CCOC(C)=O>[P:41]([O:53][CH2:54][N:10]1[CH:11]=[N:12][C:8]([C:7]2[CH:6]=[CH:5][C:4]([C:13]3[CH:14]=[N:15][N:16]4[CH:21]=[CH:20][C:19]([N:22]5[C@@H:26]([C:27]6[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=6)[CH2:25][O:24][C:23]5=[O:34])=[N:18][C:17]=34)=[CH:3][C:2]=2[F:1])=[N:9]1)([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:42]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 11701630Di-tert-butyl (chloromethyl) phosphateHCID 178519150HCID 178519150, 화합물

생성물 1

HCID 131731963(S)-di-tert-butyl (3-(2-fluoro-4-(5-(4-(5-fluoropyridin-2-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1H-1,2,4-triazol-1-yl)methyl phosphate수율 28.6%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (S)-3-(3-(3-fluoro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (0.66 g, 1.4 mmol) in DMF (10 mL) was added cesium carbonate (0.47 g, 1.4 mmol) followed by di-tert-butyl chloromethyl phosphate (1.1 g, 4.3 mmol) and the reaction mixture was stirred overnight at ambient temperature, then diluted with EtOAc (100 mL). The organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The crude material was chromatographed twice on silica gel using EtOAc as eluent to yield (S)-di-tert-butyl (3-(2-fluoro-4-(5-(4-(5-fluoropyridin-2-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1H-1,2,4-triazol-1-yl)methyl phosphate (0.27 g, 0.40 mmol, 28% yield).

후처리

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was chromatographed twice on silica gel

출처 및 근거

ORD 기록
ord-2b80775c0ffa47bea698411f43728cc2
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08865726B2

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