(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one → (5r)-3-[4-(1(r,s)-Oxo-3,6-dihydro-2h-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one

HRID 1268971노트

반응식

HRID 1268971 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]=[N+:20]=[N-:21])[O:15][C:14]3=[O:22])=[CH:9][C:8]=2[F:23])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:25].[Na+]>CO.C(OC(=O)C)C.O>[O:25]=[S:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:19]=[N+:20]=[N-:21])[O:15][C:14]3=[O:22])=[CH:9][C:8]=2[F:23])[CH2:5][CH2:6]1

참가 물질

5

반응물 2

HCID 11450455(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-oneHCID 23667635Sodium periodate

생성물 1

HCID 11371542(5r)-3-[4-(1(r,s)-Oxo-3,6-dihydro-2h-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one수율 95.7%

시약·촉매·용매 2

HCID 962Water용매HCID 21584119Ethylacetate methanol용매

실험 절차

(5R)-3-[4-(3,6-Dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one (2.3 g, 6.5 mmol) (see WO 01/81350) was dissolved in methanol/ethylacetate (1:1, 100 ml) and sodium periodate (1.75 g, 8.2 mmol) dissolved in water (20 ml) was added dropwise over 1 hour. The reaction mixture was stirred for 7 hours at room temperature, filtered to remove most of the salts and the methanol was evaporated under vacuum. The aqueous solution thus obtained was extracted with ethylacetate, dried over sodium sulfate and evaporated to dryness. The residue was subjected to chromatography on silica gel with acetone/hexane (2:1) to give 2.18 g of the product.

후처리

  1. additionwas added dropwise over 1 hour
  2. filtrationfiltered
  3. customto remove most of the salts
  4. customthe methanol was evaporated under vacuum
  5. customThe aqueous solution thus obtained
  6. extractionwas extracted with ethylacetate
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-b2777c60a80740609882b6f856a38b20
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199143B2

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