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Pyridine → (1S,6R,9aR)-6-(3,4-difluorophenyl)-1-methyltetrahydro-[1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

HRID 16387
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HRID 16387 반응식
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[NH:14][C@@H:13]([CH:15]([OH:17])[CH3:16])[CH2:12][O:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].N1C=CC=CC=1.[C:24](Cl)(=[O:28])[C:25](Cl)=[O:26]>ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:10][O:11][CH2:12][C@@H:13]3[C@H:15]([CH3:16])[O:17][C:24](=[O:28])[C:25](=[O:26])[N:14]23)[CH:5]=[CH:6][C:7]=1[F:8]
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참가 물질

6

반응물 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 673752911-[(3R,5R)-5-(3,4-difluorophenyl)morpholin-3-yl]ethanol

생성물 1

HCID 67372582(1S,6R,9aR)-6-(3,4-difluorophenyl)-1-methyltetrahydro-[1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

시약·촉매·용매 2

HCID 962Water용매
HCID 6344
Dichloromethane
용매

실험 절차

To a solution consisting of 1-[(3R,5R)-5-(3,4-difluorophenyl)morpholine-3-yl]ethanol (424 mg) and pyridine (2 mL) in dichloromethane (8 mL) was dropwise added oxalyl chloride (417 μL) while cooling with ice. The resultant solution was stirred at the same temperature for 30 minutes. The reaction solution was diluted with water, and the organic layer was partitioned. The organic layer was then dried over magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/4), to thereby obtain the titled compound (353 mg). The physical properties of the compound were as follows.

후처리

  1. temperaturewhile cooling with ice
  2. customthe organic layer was partitioned
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. customSolvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/4)

출처 및 근거

ORD 기록
ord-257e7e727ab7428bbfc3c4d84c9c9624
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737141B2

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