(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 1268971ノート

反応式

HRID 1268971 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21584119Ethylacetate methanol溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-b2777c60a80740609882b6f856a38b20
出典データセット
uspto-grants-2007_04
特許番号
US07199143B2

反応ノート

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