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, a solution of (S)-2-(benzyloxycarbonylamino)propanoic acid 33.48 g (150 mmol) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride 62.26 g (225 mmol) in acetonitrile 225 ml was added and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate 600 ml and washed with water 300 ml and brine 300 ml. The organic phase was dried over magnesium sulfate and filtered and the mother solution was concentrated in vacuo to obtain the title compound 42 g (93%).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additionthe residue was diluted with ethyl acetate 600 ml
- washwashed with water 300 ml and brine 300 ml
- dry with materialThe organic phase was dried over magnesium sulfate
- filtrationfiltered
- concentrationthe mother solution was concentrated in vacuo
Sources & evidence
- ORD record
- ord-b8f1511102584073bc39f0f310967740
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040531B2
Reaction notes
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