Sodium periodate → (R)-4-(5-bromo-2-fluoro-phenyl)-3-(2,4-dimethoxy-benzyl)-4-methyl-[1,2,3]oxathiazolidine 2,2-dioxide

HRID 920145ノート

反応式

HRID 920145 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:26])=[C:6]([C:8]2([CH3:25])[CH2:12][O:11][S@@:10](=[O:13])[N:9]2[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[O:23][CH3:24])[CH:7]=1.I([O-])(=O)(=O)=[O:28].[Na+]>C(OCC)(=O)C.C(#N)C.O.[Ru](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:26])=[C:6]([C@:8]2([CH3:25])[CH2:12][O:11][S:10](=[O:28])(=[O:13])[N:9]2[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[O:23][CH3:24])[CH:7]=1

参加物

7

反応物 2

HCID 23667635Sodium periodateHCID 90023517(R)-4-(5-bromo-2-fluoro-phenyl)-3-(2,4-dimethoxy-benzyl)-4-methyl-[1,2,3]oxathiazolidine 2-oxide

生成物 1

HCID 90016409(R)-4-(5-bromo-2-fluoro-phenyl)-3-(2,4-dimethoxy-benzyl)-4-methyl-[1,2,3]oxathiazolidine 2,2-dioxide収率 96%

試薬・触媒・溶媒 4

HCID 61850Ruthenium trichloride触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
23 °C

実験手順

To a mixture of (R)-4-(5-bromo-2-fluoro-phenyl)-3-(2,4-dimethoxy-benzyl)-4-methyl-[1,2,3]oxathiazolidine 2-oxide (15.7 g, 35.3 mmol, Eq: 1.00) and sodium periodate (8.31 g, 38.9 mmol, Eq: 1.1) in ethyl acetate (120 ml), acetonitrile (120 ml) and cold water (192 ml) at 23° C. was added ruthenium(III) chloride (73.3 mg, 353 μmol, Eq: 0.01) and this reaction mixture was stirred vigorously at 23° C. for 30 minutes. Extracted with sat NaHCO3, ethyl acetate, dried the organic layer over Na2SO4, filtered off and evaporated totally. The residue was purified by silica gel column chromatography with heptane/ethyl acetate to give the. The product fractions were collected and totally evaporated, dried in HV to give the (R)-4-(5-bromo-2-fluoro-phenyl)-3-(2,4-dimethoxy-benzyl)-4-methyl-[1,2,3]oxathiazolidine 2,2-dioxide (15.6 g, 33.9 mmol, 95.9% yield) as a white solid. MS (ISN): m/z=458.0 [M−H]− and 460.0 [M+2H]−.

後処理

  1. extractionExtracted with sat NaHCO3, ethyl acetate
  2. dry with materialdried the organic layer over Na2SO4
  3. filtrationfiltered off
  4. customevaporated totally
  5. customThe residue was purified by silica gel column chromatography with heptane/ethyl acetate
  6. customto give the
  7. customThe product fractions were collected
  8. customtotally evaporated
  9. customdried in HV

出典と根拠

ORDレコード
ord-d6b9eb88b1924ff59aa91c8be8c229d2
出典データセット
uspto-grants-2016_03
特許番号
US09273042B2

反応ノート

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