Water → (4RS,5SR)-5-(4-fluorophenyl)-4-((4-(methyloxy)phenyl)methyl)-1,3-oxazolidin-2-one

HRID 1610291ノート

反応式

HRID 1610291 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:22])[CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)C(O)=O)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[OH2:47]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:22][C:45](=[O:47])[NH:42][CH:9]2[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261867(2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(4-methoxybenzyl)propionic acid

生成物 1

HCID 22261570(4RS,5SR)-5-(4-fluorophenyl)-4-((4-(methyloxy)phenyl)methyl)-1,3-oxazolidin-2-one収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(4-methoxybenzyl)propionic acid (13.7 g, 45.0 mmol) in tetrahydrofuran (150 ml) were added diphenylphosphoryl azide (12.6 ml, 58.5 mmol) and triethylamine (8.78 ml, 63.0 mmol) and the mixture was stirred for 30 min. The mixture was further heated under reflux for 4 hrs and allowed to stand at room temperature. Water (2.00 ml) was added and the mixture was extracted with ethyl acetate (200 ml). The extract was washed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:ethyl acetate=4:1-2:1) to give (4RS,5SR)-5-(4-fluorophenyl)-4-((4-(methyloxy)phenyl)methyl)-1,3-oxazolidin-2-one (13.0 g, 96%) as crystals.

後処理

  1. temperatureThe mixture was further heated
  2. temperatureunder reflux for 4 hrs
  3. customto stand at room temperature
  4. extractionthe mixture was extracted with ethyl acetate (200 ml)
  5. washThe extract was washed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=4:1-2:1)

出典と根拠

ORDレコード
ord-afd21aa41da14ac1a23144af8c5a7e5e
出典データセット
uspto-grants-2006_01
特許番号
US06982348B2

反応ノート

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