Sodium Azide → (S)-N-[[3-[4-Azido-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1415900노트

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HRID 1415900 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[NH2:8].N([O-])=O.[Na+].[N-:24]=[N+:25]=[N-].[Na+].C([O-])(=O)C.[Na+]>Cl.O>[N:8]([C:7]1[CH:6]=[CH:5][C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])=[CH:3][C:2]=1[F:1])=[N+:24]=[N-:25]

참가 물질

7

반응물 4

HCID 33557Sodium AzideHCID 517045Sodium AcetateHCID 10778218(S)-N-[3-[3-Fluoro-4-aminophenyl]-2-oxo-5-oxazolidinyl]methylacetamideHCID 23668193Sodium Nitrite

생성물 1

HCID 10708829(S)-N-[[3-[4-Azido-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide수율 93.5%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매

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온도
0 °C

실험 절차

A solution of 4.0 g (14.96 mmol) of (S)-N-[3-[3-Fluoro-4-aminophenyl]-2-oxo-5-oxazolidinyl]methylacetamide from Example 9 in 40 mL of 6N HCl solution at 0° C. was treated portionwise with 4.12 g (59.84 mmol) of sodium nitrite, followed by stirring at 0° C. for 2 h. The mixture was then treated in several portions with a solution of 1.94 g (29.92 mmol) of sodium azide and 24.52 g (0.30 mol) of sodium acetate in in 50 mL of water. After addition was complete, solution was extracted with ethyl acetate, and the organic layer was dried (Na2SO4) and concentrated in vacuo to afford 4.1 g (93%) of the title compound as a light yellow solid, sufficiently pure for further use. 1H NMR (CDCl3) δ 8.22, 7.59, 7.33, 4.72, 4.10, 3.72, 3.40, 1.90.

후처리

  1. additionAfter addition
  2. extractionsolution was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3a8e56af3dc040a2a73f83e1ad42cae3
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05910504

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