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 the solution of N-methoxy-N-methylamine hydrochloride 21.95 g (225 mmol) in 1N sodium hydroxide 225 ml, (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 acetnitrile 225 ml were added and 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 with magnesium sulfate and filtered and the mother solution 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
- washwashed with water 300 ml and brine 300 ml
- dry with materialThe organic phase was dried with magnesium sulfate
- filtrationfiltered
- concentrationthe mother solution was concentrated in vacuo
Sources & evidence
- ORD record
- ord-f31877c0647e46dc8f85d78a03a68d1f
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193734B2
Reaction notes
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