Sodium hydride → Methyl 2-fluoro-5-nitro-3-(2-oxo-1-pyrrolidinyl)benzoate

HRID 852582ノート

反応式

HRID 852582 の反応式
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[C:9]([F:21])=[C:10]([CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:6].[H-].[Na+]>C1COCC1.CCOC(C)=O>[F:21][C:9]1[C:8]([N:7]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])=[CH:17][C:16]([N+:18]([O-:20])=[O:19])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

参加物

5

反応物 2

HCID 24758Sodium hydrideHCID 69358882Methyl 3-[(4-chlorobutanoyl)amino]-2-fluoro-5-nitrobenzoate

生成物 1

HCID 69360218Methyl 2-fluoro-5-nitro-3-(2-oxo-1-pyrrolidinyl)benzoate収率 43.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of methyl 3-[(4-chlorobutanoyl)amino]-2-fluoro-5-nitrobenzoate (D139) (8.5 g, 26.7 mmol, 1 equiv) in THF (100 ml) was added NaH (60% dispersion in mineral oil, 1.17 g, 29.4 mmol, 1.1 equiv) and the resulting mixture was stirred at room temperature for 1.5 h then diluted with AcOEt. The organic phase was washed with H2O, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 2/1) gave methyl 2-fluoro-5-nitro-3-(2-oxo-1-pyrrolidinyl)benzoate (D140) (3.3 g, 43%) as a yellow solid. [M+H]+=283.1, RT=2.53 min.

後処理

  1. washThe organic phase was washed with H2O
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 2/1)

出典と根拠

ORDレコード
ord-55f0fd4440af41af8f5e2815f87c9a9a
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

反応ノート

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