Water → HCID 66665909、化合物

HRID 406200

反応式

HRID 406200 の反応式
[Mn]([O-])(=O)(=O)=O.[K+].[C:7]1([CH3:37])[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[CH:29]=[CH:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:16]3=[N:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[CH:9][CH:8]=1.S(=O)(O)[O-:39].[Na+].[OH2:43]>[Cl-].C([N+](CCCC)(CCCC)C)CCC.C(Cl)Cl>[OH:43][CH:28]1[CH2:27][N:26]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[C:16]2=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:13]([C:10]3[CH:9]=[CH:8][C:7]([CH3:37])=[CH:12][CH:11]=3)[N:14]=[C:15]2[CH:29]1[OH:39]

参加物

7

反応物 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 66666278HCID 66666278、化合物

生成物 1

HCID 66665909HCID 66665909、化合物

試薬・触媒・溶媒 2

HCID 91822Tributylmethylammonium chloride触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of tributylmethylammonium chloride (0.970 g, 4.11 mmol) in DCM (15 ml) at RT under nitrogen was added potassium permanganate (0.650 g, 4.11 mmol) portionwise over 10 minutes. The mixture was cooled to 0° C. and treated dropwise with a solution of tert-butyl 2,3-dip-tolylpyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 2) (1 g, 2.418 mmol) in DCM (10 ml). A solution of sodium bisulfite (1.510 g, 14.51 mmol) in water (12.5 ml) was added keeping the temperature <10° C. The mixture was filtered through Celite® (filter material), washing with DCM. The phases were separated and the organic portion was washed with brine, dried (sodium sulphate), filtered and the solvent was removed in vacuo. The crude product was dissolved in DCM and purified by chromatography on silica eluting with 30-50% EtOAc in iso-hexanes to afford the title compound;

後処理

  1. customthe temperature <10° C
  2. filtrationThe mixture was filtered through Celite® (filter material)
  3. washwashing with DCM
  4. customThe phases were separated
  5. washthe organic portion was washed with brine
  6. dry with materialdried (sodium sulphate)
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. dissolutionThe crude product was dissolved in DCM
  10. custompurified by chromatography on silica eluting with 30-50% EtOAc in iso-hexanes

出典と根拠

ORDレコード
ord-5e2b1906b94441489d4cd006247cd8ce
出典データセット
uspto-grants-2014_06
特許番号
US08754085B2

関連ノート

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