Dimethylformamide → (5S)-5-(azidomethyl)-3-benzyl-1,3-oxazolidin-2-one

HRID 2066814ノート

反応式

HRID 2066814 の反応式
[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13]Cl)[O:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[N-:21]=[N+:22]=[N-:23].[Na+]>ClCCl.CO>[N:21]([CH2:13][C@H:11]1[O:10][C:9](=[O:15])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12]1)=[N+:22]=[N-:23]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 14698771HCID 14698771、化合物2 回

生成物 1

HCID 59409879(5S)-5-(azidomethyl)-3-benzyl-1,3-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
120 °C

実験手順

A 40 ml vial was charged with 3-benzyl-5-(chloromethyl)-1,3-oxazolidin-2-one (112 mg, 0.5 mmol, INTERMEDIATE 13), dimethylformamide (5 ml), and sodium azide (130 mg, 2 mmol). The mixture was heated to 120° C. for 15 h. The crude was applied to a pad of silica and washed with methanol (2×10 ml). The organics were pooled and concentrated to provide a residue. The title compound was isolated on silica gel eluting with a gradient of dichloromethane/methanol from 0% to 100% to provide 100 mg (86%) as a tan oil. Mass spectrum (ESI) 233.2 (M+1).

後処理

  1. washwashed with methanol (2×10 ml)
  2. concentrationconcentrated
  3. customto provide a residue

出典と根拠

ORDレコード
ord-25be5566f08c44b6ab49198142c9811f
出典データセット
uspto-grants-2012_10
特許番号
US08293721B2

反応ノート

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