Water → (5R)-3-[3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5-(azidomethyl)oxazolidin-2-one

HRID 1268987노트

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HRID 1268987 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][C@@H:11]1[O:15][C:14](=[O:16])[N:13]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]3)=[C:19]([F:29])[CH:18]=2)[CH2:12]1)(=O)=O.C(OCC)(=O)C.O>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[N:1]([CH2:10][C@@H:11]1[O:15][C:14](=[O:16])[N:13]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]3)=[C:19]([F:29])[CH:18]=2)[CH2:12]1)=[N+:2]=[N-:3]

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 21356562(5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-ylmethyl methanesulfonate

생성물 1

HCID 58840977(5R)-3-[3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5-(azidomethyl)oxazolidin-2-one수율 71.7%

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

Sodium azide (0.596 g, 9.08 mmol) and 18-crown-6 (0.025 g, 0.095 mmol) were added to a solution of (5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-ylmethyl methanesulfonate (WO 01/81350) (3.161 g, 8.56 mmol) in DMF (8.5 ml). The reaction mixture was heated to 90° C. under an atmosphere of nitrogen for 19 h. It was poured into a mixture of ethyl acetate and water and was extracted three times with ethyl acetate. The combined organic layers were washed once with brine, dried over sodium sulfate, filtered and the solvent was removed under vacuum to give 1.94 g of product as a white solid.

후처리

  1. extractionwas extracted three times with ethyl acetate
  2. washThe combined organic layers were washed once with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-7b032021c5a948699dc670edcba416a4
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199143B2

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