Sodium Azide → (5R)-5-(Azidomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one

HRID 2066808

反応式

HRID 2066808 の反応式
Cl[CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)[CH2:4]1.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O.O>[N:16]([CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)[CH2:4]1)=[N+:17]=[N-:18]

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 59409863(5R)-5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one2 回

生成物 1

HCID 59409901(5R)-5-(Azidomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one収率 93.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of (5R)-5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one (2.32 g, INTERMEDIATE 7) and sodium azide (1.22 g) was heated to 100° C. in 75 ml of dimethylformamide for 15 h. The mixture was then diluted with 500 ml of water and extracted with 500 ml of ethyl acetate (3×). The combined organic layers were washed with water (250 ml) and brine (250 ml). They were then dried over sodium sulfate and concentrated in vacuo to provide 2.22 g (93%) of the title compound in >95% purity via LC/MS. Mass spectrum (ESI) 254.1 (M+1).

後処理

  1. extractionextracted with 500 ml of ethyl acetate (3×)
  2. washThe combined organic layers were washed with water (250 ml) and brine (250 ml)
  3. dry with materialThey were then dried over sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-45672aaf143449068956c50a354f27d4
出典データセット
uspto-grants-2012_10
特許番号
US08293721B2

関連ノート

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