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

HRID 920145노트

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HRID 920145 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 61850Ruthenium trichloride촉매HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
23 °C

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-d6b9eb88b1924ff59aa91c8be8c229d2
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273042B2

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