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Sodium Methoxide → HCID 178462386, 화합물

HRID 1936848
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HRID 1936848 반응식
C[O-].[Na+].[F:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C@@:12]1([CH2:16][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)[C@H:14]([CH3:15])[O:13]1.C([S:25][C@@H:26]1[CH2:31][O:30][C@@H:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:28][CH2:27]1)(=O)C>CO.C(O)C>[F:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C@:12]([OH:13])([C@H:14]([S:25][C@@H:26]1[CH2:27][O:28][C@@H:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:30][CH2:31]1)[CH3:15])[CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10942334Sodium MethoxideHCID 86757717(2R,3S)-2-(2,3-Difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxiraneHCID 178477153HCID 178477153, 화합물

생성물 1

HCID 178462386HCID 178462386, 화합물수율 6.6%

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 887
Methanol
용매

실험 절차

0.29 ml (1.4 mmol) of a 4.9 M solution of sodium methoxide in methanol were added to a solution of 1.77 g (7.1 mmol) of (2R,3S)-2-(2,3-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane [prepared as described in Step 7(iv) above] and 2.20 g (9.2 mmol) of trans-5-(acetylthio)-2-phenyl-1,3-dioxane [prepared as described in Japanese Patent Application (Kokai) Hei 8-333350] in 20 ml of ethanol. The resulting mixture was then heated under reflux for 7 hours. After cooling the reaction mixture, it was partitioned between ethyl acetate and an aqueous ammonium chloride solution. The organic layer was washed with saturated aqueous sodium chloride solution and concentrated under reduced pressure to afford 3.65 g of the crude title compound. An aliquot (0.28 g) of the crude residue was purified by chromatography on a silica gel (15 g) column using a 2:5 mixture of ethyl acetate and hexane as eluent to afford 0.21 g of the title compound.

후처리

  1. temperatureThe resulting mixture was then heated
  2. temperatureunder reflux for 7 hours
  3. temperatureAfter cooling the reaction mixture, it
  4. customwas partitioned between ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride solution
  6. concentrationconcentrated under reduced pressure
  7. customto afford 3.65 g of the crude title compound
  8. customAn aliquot (0.28 g) of the crude residue was purified by chromatography on a silica gel (15 g) column
  9. additiona 2:5 mixture of ethyl acetate and hexane as eluent

출처 및 근거

ORD 기록
ord-0b2f25f4a9c1429390b86ffb98ea1d5b
출처 데이터셋
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06391903B1

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