Water → HCID 66665909, 화합물

HRID 406200

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HRID 406200 반응식
[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]

참가 물질

7

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HCID 962WaterHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 66666278HCID 66666278, 화합물

생성물 1

HCID 66665909HCID 66665909, 화합물

시약·촉매·용매 2

HCID 91822Tributylmethylammonium chloride촉매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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;

후처리

  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

출처 및 근거

ORD 기록
ord-5e2b1906b94441489d4cd006247cd8ce
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754085B2

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