Methylamine → 5-Nitrooxy-pentanoic acid methylamide
Reaction equation
[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]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
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%).
Workup
- stirringThe solution was stirred from 0° C. to RT for 18 hours
- customto dry the reaction mixture
- filtrationThe resulting mixture was filtered off
- concentrationthe filtrate was concentrated under vacuum
- custompurified by flash chromatography [Biotage®, dichloromethane/methanol 100/0→97/3 (15CV*)]
Sources & evidence
- ORD record
- ord-c928b5ee08bd4c14b6c44a42f20b721c
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365489B2
Reaction notes
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