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

HRID 1955114ノート

反応式

HRID 1955114 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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) δ8.22, 7.59, 7.33, 4.72, 4.10, 3.72, 3.40, 1.90.

後処理

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

出典と根拠

ORDレコード
ord-3bd32f29fa204163bfe6b2514156419d
出典データセット
uspto-grants-2000_09
特許番号
US06124334

反応ノート

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