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

HRID 852582노트

반응식

HRID 852582 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-55f0fd4440af41af8f5e2815f87c9a9a
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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