Methylamine → 5-Nitrooxy-pentanoic acid methylamide

HRID 1625584ノート

反応式

HRID 1625584 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-5b1d2ee120794cc3b6c9b59b5baa7bed
出典データセット
uspto-grants-2014_07
特許番号
US08784871B2

反応ノート

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