Sodium Bicarbonate → (5R)-3-(3-Fluoro-4-(2-methylimidazol-1-yl)phenyl)-5-hydroxymethyloxazolidin-2-one

HRID 723772

반응식

HRID 723772 반응식
C(O[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([N:19]2[CH:23]=[CH:22][N:21]=[C:20]2[CH3:24])=[C:16]([F:18])[CH:17]=1)=O)C1C=CC=CC=1.C([Li])CCC.[CH2:30]([O:34][C:35](=[O:39])CCC)[C@@H:31]1[O:33]C1.C(=O)(O)[O-].[Na+]>O1CCCC1.CN1CCCN(C)C1=O.C(OCC)(=O)C>[F:18][C:16]1[CH:17]=[C:12]([N:11]2[CH2:9][C@H:30]([CH2:31][OH:33])[O:34][C:35]2=[O:39])[CH:13]=[CH:14][C:15]=1[N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH3:24]

참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 218766515-Benzyloxycarbonylamino-2-(2-methyl-imidazol-1-yl)fluorobenzeneHCID 178418339Butyllithium

생성물 1

HCID 21356557(5R)-3-(3-Fluoro-4-(2-methylimidazol-1-yl)phenyl)-5-hydroxymethyloxazolidin-2-one수율 44.5%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

실험 절차

5-Benzyloxycarbonylamino-2-(2-methylimidazol-1-yl)fluorobenzene (54 g, 0.166 M) was dissolved in a mixture of dry tetrahydrofuran (600 ml) and 1,3-dimethyl-tetrahydropyrimidin-2-one (100 ml) under nitrogen, cooled to −70°, and treated with a solution of n-butyllithium (1.6M in isohexane, 114 ml), over 30 minutes. After stirring for 30 minutes at −70°, a solution of (R)-glycidylbutyrate (26.35 g, 0.183 M) in dry tetrahydrofuran (50 ml) was added over 15 minutes. Stirring was continued for 16 hours allowing the temperature to rise to ambient. The mixture was treated with aqueous sodium bicarbonate (5%, 500 ml) and ethyl acetate (800 ml), the organic layer separated, and the aqueous extracted with further ethyl acetate (3×750 ml). The combined extracts were dried (magnesium sulfate) and evaporated, and the resulting oil triturated with diethyl ether. The resulting solid was recrystallisd from isopropanol to give the title compound (21.5 g).

후처리

  1. temperaturecooled to −70°
  2. stirringStirring
  3. waitwas continued for 16 hours
  4. customthe organic layer separated
  5. extractionthe aqueous extracted with further ethyl acetate (3×750 ml)
  6. dry with materialThe combined extracts were dried (magnesium sulfate)
  7. customevaporated
  8. customthe resulting oil triturated with diethyl ether

출처 및 근거

ORD 기록
ord-c1d982bee00542ee9f3a54dcce596308
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141583B2

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