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Sodium Azide → (5R)-5-azidomethyl-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one

HRID 1108582
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HRID 1108582 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22]OS(C)(=O)=O)[O:19][C:18]2=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[C:10](=[O:16])[CH2:9]1.[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C>[N:29]([CH2:22][C@@H:20]1[O:19][C:18](=[O:28])[N:17]([C:4]2[CH:5]=[CH:6][C:7]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[C:10](=[O:16])[CH2:9]3)=[C:2]([F:1])[CH:3]=2)[CH2:21]1)=[N+:30]=[N-:31]
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참가 물질

4

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HCID 33557Sodium AzideHCID 53790592(5R)-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)-oxazolidin-2-one

생성물 1

HCID 53831456(5R)-5-azidomethyl-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one수율 93.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

(5R)-3-(3-Fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)-oxazolidin-2-one (950 mg) was dissolved in dry DMF (30 ml) and sodium azide (893 mg) was added. The mixture was heated at 80° C. for 5 hours, and then evaporated to dryness. The residue was dissolved in ethyl acetate and the resulting solution washed with water and dried (MgSO4). The crude product so obtained was chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 6% methanol in dichloromethane. Relevant fractions were combined and evaporated to give (5R)-5-azidomethyl-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one (777 mg).

후처리

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe resulting solution washed with water
  4. dry with materialdried (MgSO4)
  5. customThe crude product so obtained
  6. customwas chromatographed on silica
  7. temperaturea gradient increasing in polarity from 0 to 6% methanol in dichloromethane
  8. customevaporated

출처 및 근거

ORD 기록
ord-46b7265681934031ac0c0f6eddd1ef5d
출처 데이터셋
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06069145

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