(4R)-4-phenyl-1,3-oxazolidin-2-one → 3-[(2-fluorophenyl)-acetyl]-4(R)-phenyl-2-oxazolidinone

HRID 566261

反応式

HRID 566261 の反応式
[C:1]1([C@@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26](Cl)=[O:27]>C1COCC1>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([N:8]1[C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][O:10][C:9]1=[O:12])=[O:27]

参加物

5

反応物 3

HCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-oneHCID 140040112-(2-Fluorophenyl)acetyl chlorideHCID 178418339Butyllithium

生成物 1

HCID 111506973-[(2-fluorophenyl)-acetyl]-4(R)-phenyl-2-oxazolidinone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a −78° C. solution of 4(R)-phenyl-2-oxazolidinone (340 g, 2.08 mol) in THF (8000 mL), is added n-BuLi (2.5 M, 920 mL, 1.1 eq). The reaction mixture is stirred for 20 minutes and 2-fluorobenzeneacetyl chloride (358 g, 2.08 mol) is added. After 2 hours the reaction mixture is quenched with saturated NH4Cl solution (1×1000 mL). The organic layer is separated, washed with H2O (1×1000 mL), saturated NaCl solution (2×1000 mL) and then concentrated in vacuo. This procedure yields 3-[(2-fluorophenyl)-acetyl]-4(R)-phenyl-2-oxazolidinone.

後処理

  1. customAfter 2 hours the reaction mixture is quenched with saturated NH4Cl solution (1×1000 mL)
  2. customThe organic layer is separated
  3. washwashed with H2O (1×1000 mL), saturated NaCl solution (2×1000 mL)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a69ac4c89f1d4bc4a721bb5b827e620f
出典データセット
uspto-grants-2001_01
特許番号
US06174888B1

関連ノート

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