Methylamine → 5-Nitrooxy-pentanoic acid methylamide

HRID 2201607ノート

反応式

HRID 2201607 の反応式
[N+:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)([O-:3])=[O:2].[CH2:12]([N:14](CC)CC)C.ClC(OCC)=O.CN.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl>[CH3:12][NH:14][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][O:4][N+:1]([O-:3])=[O:2]

参加物

7

反応物 5

HCID 6329MethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 24436Sodium SulfateHCID 117884725-nitrooxypentanoic Acid

生成物 1

HCID 716186675-Nitrooxy-pentanoic acid methylamide収率 47%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of compound 2 (1.60 g, 1.0 eq) in dry dichloromethane (20.0 mL) cooled to 0° C. was added triethylamine (1.70 mL, 1.2 eq) followed by ethyl chloroformate (1.10 mL, 1.1 eq). The reaction mixture was stirred at 0° C. for 45 minutes and 40% aqueous methyl amine (20.0 mL) was added. The solution was stirred from 0° C. to RT for 18 hours and sodium sulphate was added to dry the reaction mixture. The resulting mixture was filtered off and the filtrate was concentrated under vacuum. The residue was adsorbed on silica gel and purified by flash chromatography [Biotage®, dichloromethane/methanol 100/0→97/3 (15CV*)] affording compound 3 as a colourless liquid (0.84 g, yield=47%).

後処理

  1. stirringThe solution was stirred from 0° C. to RT for 18 hours
  2. customto dry the reaction mixture
  3. filtrationThe resulting mixture was filtered off
  4. concentrationthe filtrate was concentrated under vacuum
  5. custompurified by flash chromatography [Biotage®, dichloromethane/methanol 100/0→97/3 (15CV*)]

出典と根拠

ORDレコード
ord-c928b5ee08bd4c14b6c44a42f20b721c
出典データセット
uspto-grants-2016_06
特許番号
US09365489B2

反応ノート

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