(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one → (5r)-3-[3-Fluoro-4-(1 (r,s)-oxo-3,6-dihydro-2h-thiopyran-4-yl)phenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723805노트

반응식

HRID 723805 반응식
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:19]4[CH:23]=[CH:22][N:21]=[N:20]4)[O:15][C:14]3=[O:24])=[CH:9][C:8]=2[F:25])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:27].[Na+]>CO.C(OCC)(=O)C.O>[F:25][C:8]1[CH:9]=[C:10]([N:13]2[CH2:17][C@H:16]([CH2:18][N:19]3[CH:23]=[CH:22][N:21]=[N:20]3)[O:15][C:14]2=[O:24])[CH:11]=[CH:12][C:7]=1[C:4]1[CH2:5][CH2:6][S:1](=[O:27])[CH2:2][CH:3]=1

참가 물질

6

반응물 2

HCID 11302859(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-oneHCID 23667635Sodium periodate

생성물 1

HCID 11451677(5r)-3-[3-Fluoro-4-(1 (r,s)-oxo-3,6-dihydro-2h-thiopyran-4-yl)phenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one수율 87.4%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one (Example 83; 1.25 g, 3.5 mmol) was stirred in a mixture of methanol and ethyl acetate (1:1, 50 ml) at ambient temperature. Sodium periodate (0.93 g, 4.3 mmol) in water (10 ml) was added dropwise, and it was stirred for 18 hours. Precipitated salts were removed by filtration and solvents were removed under vacuum. The residue was chromatographed on silica gel, washing with 25% acetone in dichloromethane, then eluting with 5 to 7% methanol in dichloromethane to give the title product (1.152 g).

후처리

  1. customPrecipitated salts were removed by filtration and solvents
  2. customwere removed under vacuum
  3. customThe residue was chromatographed on silica gel
  4. washwashing with 25% acetone in dichloromethane
  5. washeluting with 5 to 7% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-f752ca4ffba34a81b583cd02910d6f3d
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141583B2

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