Trifluoroacetic acid → (2S,4S)-Methyl 2-amino-4-phenylhexanoate
Reaction equation
FC(F)(F)C(O)=[O:4].C([C@@H]1C(OC)=[N:15][C@@H:14]([CH2:19][C@@H:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH3:22])[C:13]([O:29][CH3:30])=N1)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>O.C(#N)C>[CH3:30][O:29][C:13](=[O:4])[C@@H:14]([NH2:15])[CH2:19][C@@H:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:21][CH3:22]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of trifluoroacetic acid (3.4 ml) in water (440 ml) was added dropwise over 15 min a solution of (2R,5S)-2-isopropyl-3,6-dimethoxy-5-((S)-2-phenyl-butyl)-2,5-dihydro-pyrazine (4.69 g, 14.8 mmol) in acetonitrile (75 ml). The mixture was stirred overnight at room temperature then made basic by addition of saturated aqueous sodium carbonate solution and the mixture was extracted with ethyl acetate. The phases were separated and the organic phase was washed sequentially with water and with saturated brine, then dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, EtOAc/heptane) to yield a yellow oil (2.78 g, 85%); MS (ISP): 222.1 ([M+H]+).
Workup
- extractionthe mixture was extracted with ethyl acetate
- customThe phases were separated
- washthe organic phase was washed sequentially with water and with saturated brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography (SiO2, EtOAc/heptane)
Sources & evidence
- ORD record
- ord-7af8b51afbe44b5a8212f34f3f4933a6
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604061B2
Reaction notes
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