Water → benzyl N-[4-(2-azidoethyl)piperidine-1-carboximidoyl]carbamate

HRID 1610802

反応式

HRID 1610802 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21]OS(C)(=O)=O)[CH2:16][CH2:15]1)=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:27]=[N+:28]=[N-:29].[Na+].O>CN(C)C=O>[N:27]([CH2:21][CH2:20][CH:17]1[CH2:18][CH2:19][N:14]([C:12](=[NH:13])[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:15][CH2:16]1)=[N+:28]=[N-:29]

参加物

5

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 1403790842-[1-(N-phenylmethoxycarbonylcarbamimidoyl)piperidin-4-yl]ethyl methanesulfonate

生成物 1

HCID 140379074benzyl N-[4-(2-azidoethyl)piperidine-1-carboximidoyl]carbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

In 100 ml of dimethylformamide was dissolved 4.4 g (0.0115 mol) of crude 1-benzyloxycarbonylamidino-4-mesyloxyethyl piperidine and 4.5 g (0.069 Mol) of sodium azide was added. The mixture was heated at 100° C. for 2.5 h. It was then poured into water and extracted with ethyl acetate three times. The combined organic phase was washed with water, dried (Na2SO4) and evaporated. The residue was flash chromatographed on silica gel using ethyl acetate/heptane 1/1 as eluent. Yield: 3.0 g (79%).

後処理

  1. additionwas added
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customchromatographed on silica gel

出典と根拠

ORDレコード
ord-a73614eb32cd4e089303c1e43a2034d0
出典データセット
uspto-grants-2006_01
特許番号
US06984627B1

関連ノート

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