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

HRID 1108573ノート

反応式

HRID 1108573 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[CH:7]=[C:8]([N:20]2[CH2:24][C@H:23]([CH2:25]OS(C)(=O)=O)[O:22][C:21]2=[O:31])[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[CH2:13]1>CN(C=O)C.C(OCC)(=O)C>[N:1]([CH2:25][C@@H:23]1[O:22][C:21](=[O:31])[N:20]([C:8]2[CH:9]=[CH:10][C:11]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[CH2:13]3)=[C:6]([F:5])[CH:7]=2)[CH2:24]1)=[N+:2]=[N-:3]

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 54244897(5R)-3-(3-fluoro-4-{4-methyl-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)oxazolidin-2-one

生成物 1

HCID 11024490(5R)-5-azidomethyl-3-(3-fluoro-4-{4-methyl-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

Sodium azide (924 mg) was added to a solution of (5R)-3-(3-fluoro-4-{4-methyl-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)oxazolidin-2-one (950 mg) in dry DMF (50 ml), and the mixture heated at 75° C. for 2 hours. The mixture was diluted with ethyl acetate and washed with three portions of water. The aqueous layer was then 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-methyl-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one product which was used without further purification.

後処理

  1. washwashed with three portions of water
  2. extractionThe aqueous layer was then back-extracted with two portions of ethyl acetate
  3. dry with materialthe combined organic extracts dried over MgSO4
  4. customEvaporation

出典と根拠

ORDレコード
ord-403eb9b6f5d74f4cb10f3c5219b29b47
出典データセット
uspto-grants-2000_05
特許番号
US06069145

反応ノート

読み込み中…