Dimethylformamide → N-(6-Chloro-3-nitro-2-pyridyl)-alanine methyl ester
Reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6].C(N(CC)CC)C.Cl[C:17]1([N+:24]([O-:26])=[O:25])[CH:22]=[CH:21]C=C(Cl)N1.[CH3:27][N:28]([CH:30]=O)C>>[CH3:2][O:3][C:4](=[O:8])[C@@H:5]([NH:6][C:30]1[C:17]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:27]([Cl:1])[N:28]=1)[CH3:7]Participants
5
Procedure
To a solution of L-alanine-methyl ester hydrochloride (1.68 g, 12.0 mmol, 1.1 equiv) and triethylamine (3.32 mL, 24.0 mmol 2.2 equiv) in DMF (20 mL) was added a solution of 2,6-dichloro-2-nitro-pyridine (2.14 g, 11.0 mmol, 1.0 equiv) in DMF (6 mL) and the reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was poured onto water and the product was extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-30%) to afford (S)-2-(6-chloro-3-nitro-pyridin-2-ylamino)-propionic acid methyl ester (1.9 g). MS: [M+H]+=260.
Workup
- additionThe reaction mixture was poured onto water
- extractionthe product was extracted with EtOAc
- washThe organic phase was washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-30%)
Sources & evidence
- ORD record
- ord-ec2d6763971d464eae43f505e74a19ad
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09155743B2
Reaction notes
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