Pyridine → 3-(4(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one

HRID 8175ノート

反応式

HRID 8175 の反応式
Cl.N1([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:17][C:16]3=[O:25])=[CH:10][C:9]=2[F:26])CCC=CC1.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:33][C:34]1([CH3:42])[O:38][C@H:37]([C:39](Cl)=[O:40])[CH2:36][O:35]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:33][C:34]1([CH3:42])[O:38][C@H:37]([C:39]([N:27]2[CH2:32][CH2:31][C:30]([C:8]3[C:9]([F:26])=[CH:10][C:11]([N:15]4[CH2:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:17][C:16]4=[O:25])=[CH:12][C:13]=3[F:14])=[CH:29][CH2:28]2)=[O:40])[CH2:36][O:35]1

参加物

6

反応物 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 10374773HCID 10374773、化合物HCID 695850403-(4-(1,2,5,6-tetrahydropyridyl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one hydrochloride

生成物 1

HCID 207256423-(4(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one収率 97.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

3-(4-(1,2,5,6-tetrahydropyridyl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one hydrochloride (14.5 g, 37.3 mM) was suspended in dry dichloromethane (300 ml) under nitrogen at 0°, and treated with pyridine (9.78 g, 0.12 M). A solution of 2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride (9.59 g, 75.6 mM) in dichloromethane (100 ml) was added dropwise, and stirring continued for 3 hours, allowing the temperature to rise to ambient. Aqueous sodium bicarbonate (5%, 300 ml) was added, and stirring continued for 30 minutes. The organic phase was separated, dried (magnesium sulfate), filtered, and evaporated to dryness after the addition of toluene (20 ml). The solid residue was triturated with a mixture of diethyl ether (250 ml) and isohexane (150 ml), and solid filtered to give the title compound (17.5 g).

後処理

  1. stirringstirring
  2. waitcontinued for 30 minutes
  3. customThe organic phase was separated
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. additionafter the addition of toluene (20 ml)
  8. customThe solid residue was triturated with a mixture of diethyl ether (250 ml) and isohexane (150 ml), and solid
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-22258999a9794eeb9e7c66c8a3b3f6bc
出典データセット
uspto-grants-2006_08
特許番号
US07087629B2

反応ノート

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