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

HRID 1108590
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HRID 1108590 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:19]2[CH2:23][C@H:22]([CH2:24]OS(C)(=O)=O)[O:21][C:20]2=[O:30])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][CH3:17])[C:10](=[O:18])[CH2:9]1.[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C=O)C>[N:31]([CH2:24][C@@H:22]1[O:21][C:20](=[O:30])[N:19]([C:4]2[CH:5]=[CH:6][C:7]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][CH3:17])[C:10](=[O:18])[CH2:9]3)=[C:2]([F:1])[CH:3]=2)[CH2:23]1)=[N+:32]=[N-:33]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

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HCID 33557Sodium AzideHCID 54157662(5R)-3-(3-fluoro-4-{4-(2-methoxyethyl)-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)oxazolidin-2-one

생성물 1

HCID 53675945(5R)-5-Azidomethyl-3-(3-fluoro-4-{4-(2-methoxyethyl)-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one수율 88.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

(5R)-3-(3-Fluoro-4-{4-(2-methoxyethyl)-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyl-oxymethyl)oxazolidin-2-one (990 mg) was dissolved in dry DMF (30 ml), sodium azide (868 mg) was added, and the mixture heated at 80° C. for 4 hours. The mixture was evaporated to dryness, and the residue dissolved in ethyl acetate and washed with three portions of water. The aqueous layer was back-extracted with two portions of ethyl acetate, and the combined organic extracts dried over MgSO4. Evaporation gave (5R)-5-azidomethyl-3-(3-fluoro-4-{4-(2-methoxyethyl)-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one (770 mg) which was used without further purification.

후처리

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with three portions of water
  4. extractionThe aqueous layer was back-extracted with two portions of ethyl acetate
  5. dry with materialthe combined organic extracts dried over MgSO4
  6. customEvaporation

출처 및 근거

ORD 기록
ord-80a9cc40f07c4270bcabc531b0b991a2
출처 데이터셋
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06069145

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