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Sodium Azide → (5R)-5-(Azidomethyl)-3-[3-Fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-1,3-oxazolidin-2-one

HRID 1452571
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HRID 1452571 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19]S(C)(=O)=O)[O:16][C:15]2=[O:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]1.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[N:25]([CH2:19][C@@H:17]1[O:16][C:15](=[O:24])[N:14]([C:4]2[CH:5]=[CH:6][C:7]([N:8]3[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]3)=[C:2]([F:1])[CH:3]=2)[CH2:18]1)=[N+:26]=[N-:27]
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참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 68879798(5R)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-[methanesulfonylmethyl]oxazolidin 2-one2회

생성물 1

HCID 57526997(5R)-5-(Azidomethyl)-3-[3-Fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-1,3-oxazolidin-2-one수율 95.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

(5R)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-[(methanesulfonyl)methyl]-oxazolidin 2-one (Intermediate 18) (5.0 g, 13.5 mmol) was dissolved in DMF (45 ml). Sodium azide (1.75 g, 27.0 mmol) was added and the reaction mixture was stirred at 70° C. for one hour. It was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic phase was washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure to give the product as a white solid (4.1 g), which was used without further purification.

후처리

  1. customIt was partitioned between ethyl acetate and saturated sodium bicarbonate
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-639790482e9b4142a2207ec530bf8921
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07473699B2

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