Acetone → (R)-2,2-diallyl-5-(5-bromo-2-fluoro-phenyl)-4-(2,4-dimethoxy-benzyl)-5-methyl-1,1-dioxo-1lambda6-thiomorpholin-3-one

HRID 920158ノート

反応式

HRID 920158 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:29])=[C:6]([C@@:8]2([CH3:28])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=3[O:23][CH3:24])[C:12](=[O:25])[CH2:11][S:10](=[O:27])(=[O:26])[CH2:9]2)[CH:7]=1.[CH2:30](Br)[CH:31]=[CH2:32].C(=O)([O-])[O-].[K+].[K+].[CH3:40][C:41]([CH3:43])=O>>[CH2:30]([C:11]1([CH2:43][CH:41]=[CH2:40])[S:10](=[O:26])(=[O:27])[CH2:9][C@:8]([C:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[F:29])([CH3:28])[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[O:23][CH3:24])[C:12]1=[O:25])[CH:31]=[CH2:32]

参加物

5

反応物 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 90067087(R)-5-(5-bromo-2-fluoro-phenyl)-4-(2,4-dimethoxy-benzyl)-5-methyl-1,1-dioxo-1lambda6-thiomorpholin-3-one

生成物 1

HCID 90067160(R)-2,2-diallyl-5-(5-bromo-2-fluoro-phenyl)-4-(2,4-dimethoxy-benzyl)-5-methyl-1,1-dioxo-1lambda6-thiomorpholin-3-one収率 53.2%

実験手順

To a solution of (R)-5-(5-bromo-2-fluoro-phenyl)-4-(2,4-dimethoxy-benzyl)-5-methyl-1,1-dioxo-1λ6-thiomorpholin-3-one (1 g, 2.06 mmol, Eq: 1.00) in acetone (8 ml) was added allyl bromide (547 mg, 391 μl, 4.52 mmol, Eq: 2.2), then potassium carbonate (853 mg, 6.17 mmol, Eq: 3.0). The reaction suspension was stirred in a sealed tube for 4 days. Extracted with water and ethyl acetate, the organic layer was separated, dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed on 20 g silica gel with 0% to 50% ethyl acetate in heptane to give (R)-2,2-diallyl-5-(5-bromo-2-fluoro-phenyl)-4-(2,4-dimethoxy-benzyl)-5-methyl-1,1-dioxo-1λ6-thiomorpholin-3-one (620 mg, 1.09 mmol, 53.2% yield) as a white foam. MS (ISP): m/z=566.2 [M+H]+ and 568.1 [M+2+H]+.

後処理

  1. extractionExtracted with water and ethyl acetate
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was chromatographed on 20 g silica gel with 0% to 50% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-d708694372ee4b4ebe96fa9e3de4208b
出典データセット
uspto-grants-2016_03
特許番号
US09273042B2

反応ノート

読み込み中…