Pyridine → (6R,9aR)-1,1-dimethyl-6-(3,4,5-trifluorophenyl)tetrahydro [1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

HRID 16392노트

반응식

HRID 16392 반응식
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[NH:15][C@@H:14]([C:16]([OH:19])([CH3:18])[CH3:17])[CH2:13][O:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].N1C=CC=CC=1.[C:26](Cl)(=[O:30])[C:27](Cl)=[O:28]>C(Cl)(Cl)Cl.O>[CH3:18][C:16]1([CH3:17])[C@H:14]2[CH2:13][O:12][CH2:11][C@@H:10]([C:4]3[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=3)[N:15]2[C:27](=[O:28])[C:26](=[O:30])[O:19]1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 673733842-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]propane-2-ol

생성물 1

HCID 67373385(6R,9aR)-1,1-dimethyl-6-(3,4,5-trifluorophenyl)tetrahydro [1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

실험 절차

To a solution of 2-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]propane-2-ol (330 mg) and pyridine (2 mL) in chloroform (10 mL) was dropwise added oxalyl chloride (205 μL) while cooling with ice. The resultant solution was stirred at the same temperature for 1 hour, and then stirred for another 2 hours at room temperature. The resultant solution was diluted with water, and the organic layer was partitioned. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure. The resultant residue was purified by silica gel column chromatography (heptane/ethyl acetate), to thereby obtain the titled compound (260 mg). The physical properties of this crude product were as follows.

후처리

  1. temperaturewhile cooling with ice
  2. customthe organic layer was partitioned
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSolvent was removed by distillation under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography (heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-4fd20f8db3314aaea9b31d5fcab683e4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737141B2

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