Dimethyl Sulfide → Epothilone A

HRID 392472

반응식

HRID 392472 반응식
[CH3:1][C:2]1[S:6][CH:5]=[C:4](/[CH:7]=[C:8](/[C@H:10]2[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[C:22]([CH3:30])([CH3:29])[C:20](=[O:21])[C@H:19]([CH3:31])[C@@H:18]([OH:32])[C@@H:17]([CH3:33])[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12][CH2:11]2)\[CH3:9])[N:3]=1.C(C(C)=[O:39])(F)(F)F.OS([O-])(=O)=O.[K+].C([O-])(O)=O.[Na+].CSC>CC#N.C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=O.[Na+].[Na+].O>[CH3:1][C:2]1[S:6][CH:5]=[C:4](/[CH:7]=[C:8](/[C@H:10]2[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[C:22]([CH3:30])([CH3:29])[C:20](=[O:21])[C@H:19]([CH3:31])[C@@H:18]([OH:32])[C@@H:17]([CH3:33])[CH2:16][CH2:15][CH2:14][C@H:13]3[O:39][C@H:12]3[CH2:11]2)\[CH3:9])[N:3]=1

참가 물질

9

반응물 5

HCID 1068Dimethyl SulfideHCID 9871Methyl trifluoromethyl ketoneHCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 9891226Epothilone C

생성물 1

HCID 448799Epothilone A수율 57%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8759EDTA disodium salt용매

실험 절차

To solution of epothilone C (100 mg, 0.21 mmol) in CH3CN (2.5 mL) and 0.0004 M Na2EDTA (1.5 ml) at 0° C. were added excess CF3COCH3 (1 mL) followed by 2 KHSO5.KHSO4.K2SO4 (potassium peroxymonosulfate) (325 mg, 0.53 mmol) and NaHCO3 (75 mg, 0.89 mmol). The reaction mixture was stirred for 35 min then treated with dimethylsulfide (0.50 mL) and water (3.75 mL). The reaction mixture was warmed to room temperature, extracted with EtOAc (4×10 mL), dried over MgSO4, filtered, and concentrated. The residue was chromatographed with 55% EtOAc/hexanes to give epothilone A (59 mg, 57%) and compound A (30 mg, 29%) as a white solid. m/z: 494(M+H)+.

후처리

  1. extractionextracted with EtOAc (4×10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed with 55% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-0a21c547423249eeab153057c21af7e4
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800653B2

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