Sodium hydride → HCID 67114136, 화합물

HRID 1968868노트

반응식

HRID 1968868 반응식
[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]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 86761808HCID 86761808, 화합물

생성물 1

HCID 67114136HCID 67114136, 화합물수율 18.3%

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-9c31f9fc882c4a23a89a9224f765cd5e
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426414B2

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