Sodium hydride → HCID 67114136、化合物

HRID 1968868ノート

反応式

HRID 1968868 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(OCC)=O)C.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]2[CH2:28]O2)[N:21]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[C:15]([O:14][C:12]([C@@H:11]1[CH2:28][C@H:26]1[C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([F:19])[N:21]=1)=[O:13])([CH3:16])([CH3:17])[CH3:18]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 86761808HCID 86761808、化合物

生成物 1

HCID 67114136HCID 67114136、化合物収率 18.3%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of NaH (60% oil dispersion, 320 mg, 8 mmol) in toluene (10 mL) was added dropwise t-butyl diethylphosphonoacetate (1.92 g, 7.6 mmol). The resulting mixture was stirred at rt for 10 min., then a solution of 2-fluoro-6-oxiranyl-pyridine (530 mg, 3.8 mmol) in toluene (5 mL) was added dropwise to the reaction mixture. The resulting mixture was then heated at reflux for 12 h. The mixture was cooled to rt and diluted with EtOAc and washed with NH4Cl (saturated) and water. The EtOAc layer was dried (Na2SO4). The solvent was removed and the residue was subjected to ISCO (40 g column, hexane 3 min. then 0-60% EtOAc in hexane over 60 min.) to give the desired product (165 mg). MS (MH+ 238).

後処理

  1. temperatureThe resulting mixture was then heated
  2. temperatureat reflux for 12 h
  3. temperatureThe mixture was cooled to rt
  4. washwashed with NH4Cl (saturated) and water
  5. dry with materialThe EtOAc layer was dried (Na2SO4)
  6. customThe solvent was removed
  7. custom40 g column, hexane 3 min.

出典と根拠

ORDレコード
ord-9c31f9fc882c4a23a89a9224f765cd5e
出典データセット
uspto-grants-2013_04
特許番号
US08426414B2

反応ノート

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