Methanamine, N-methoxy-, hydrochloride (1:1) → (S)-Benzyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate
Reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].[CH2:6]([O:13][C:14]([NH:16][C@@H:17]([CH3:21])[C:18]([OH:20])=O)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>[OH-].[Na+].C(#N)C>[CH3:2][O:3][N:4]([CH3:5])[C:18](=[O:20])[C@@H:17]([NH:16][C:14](=[O:15])[O:13][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:21]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N-methoxy-N-methylamine hydrochloride (21.95 g, 225 mmol) in 1N sodium hydroxide (225 ml) were added (S)-2-(benzyloxycarbonylamino)propanoic acid (33.48 g, 150 mmol) and a solution of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (62.26 g, 225 mmol) in acetnitrile (225 ml) and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (600 ml) and the mixture was washed with water (300 ml) and brine (300 ml). The organic layer was dried over magnesium sulfate and filtered and the filtrate was concentrated in vacuo to obtain (S)-benzyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (42.33 g, 93%).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additionthe residue was diluted with ethyl acetate (600 ml)
- washthe mixture was washed with water (300 ml) and brine (300 ml)
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-a0122d2e0fb2485d91ca1744a2262c8f
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691819B2
Reaction notes
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