Dimethyl Sulfoxide → (R)-3-(2-fluoropyrimidin-4-yl)-4-((R)-1-methoxyethyl)oxazolidin-2-one

HRID 57348ノート

反応式

HRID 57348 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([C@H:13]([O:15][CH3:16])[CH3:14])[CH2:11][O:10][C:9]2=[O:17])[CH:5]=[CH:4][N:3]=1.[F-:18].[K+].CS(C)=O>O>[F:18][C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([C@H:13]([O:15][CH3:16])[CH3:14])[CH2:11][O:10][C:9]2=[O:17])[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 522689Potassium FluorideHCID 90415843(R)-3-(2-chloropyrimidin-4-yl)-4-((R)-1-methoxyethyl)oxazolidin-2-one

生成物 1

HCID 90416779(R)-3-(2-fluoropyrimidin-4-yl)-4-((R)-1-methoxyethyl)oxazolidin-2-one収率 87.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

To a microwe vial with stir bar was added (R)-3-(2-chloropyrimidin-4-yl)-4-((R)-1-methoxyethyl)oxazolidin-2-one (145 mg, 0.56 mmol), potassium fluoride (327 mg, 5.63 mmol) and DMSO (4 mL). Vial capped and heated to 120° C. in a sand bath for 3 hr. Reaction mixture was then cooled to room temperature, diluted with water and aqueous mixture extracted with EtOAc. The Organic phases were combined and washed with water, brine, dried (Na2SO4), filtered and concentrated to afford a white crystalline of (R)-3-(2-fluoropyrimidin-4-yl)-4-((R)-1-methoxyethyl)oxazolidin-2-one (117 mg, 0.49 mmol, 86% yield). LCMS m/z 242.1 (M+H)+, Rt 0.63 min.

後処理

  1. customVial capped
  2. customReaction mixture
  3. temperaturewas then cooled to room temperature
  4. extractionextracted with EtOAc
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-6258fd54faf349dea27c33630c073763
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

反応ノート

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