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

HRID 723776

反応式

HRID 723776 の反応式
C(O[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([N:19]2[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]2)=[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]=[C:22]([CH3:24])[N:21]=[CH:20]1

参加物

8

反応物 4

HCID 516892Sodium BicarbonateHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 218766725-Benzyloxycarbonylamino-2-(4-methylimidazol-1-yl)fluorobenzeneHCID 178418339Butyllithium

生成物 1

HCID 21356561(5R)-3-(3-Fluoro-4-(4-methylimidazol-1-yl)phenyl)-5-hydroxymethyloxazolidin-2-one収率 33.7%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

実験手順

5-Benzyloxycarbonylamino-2-(4-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), and undissolved solid was removed and washed well with diethyl ether to give title product (16.3 g).

後処理

  1. temperaturecooled to −70°
  2. stirringStirring
  3. waitwas continued for 16 hours
  4. customwas removed
  5. washwashed well with diethyl ether

出典と根拠

ORDレコード
ord-ad2948a847b84777aec57417aa43b8af
出典データセット
uspto-grants-2006_11
特許番号
US07141583B2

関連ノート

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