Dimethyl Sulfide → Epothilone A

HRID 392472

反応式

HRID 392472 の反応式
[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

参加物

9

反応物 5

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

生成物 1

HCID 448799Epothilone A収率 57%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8759EDTA disodium salt溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-0a21c547423249eeab153057c21af7e4
出典データセット
uspto-grants-2004_10
特許番号
US06800653B2

関連ノート

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