Reaction equation
[CH3:1][O:2][C:3](=[O:9])[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH2:5].CN1CCOCC1.CCN=C=NCCCN(C)C.Cl.[C:29](O)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:9])[C:4]([NH2:5])([C:29]([C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=[O:36])[CH:6]([CH3:8])[CH3:7]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of L-valine methylester (3.0 g, 2.29 mmol), in DCM (30 mL) were added N-methyl morpholine (11.5 mL, 11.45 mmol), EDCI.HCl (8.7 g, 45.8 mmol) and nicotinic acid (3.3 g, 27.4 mmol). The mixture was allowed to stir at room temperature (25° C.) over 3 h under nitrogen atmosphere. The resulting mixture was diluted with ethyl acetate (200 mL), washed with water (3×100mL) and dried over sodium sulphate. The crude product obtained upon evaporation of the solvent was further purified by silica gel column chromatography to obtain required product as sticky solid (2.0 g, 38%).
Workup
- washwashed with water (3×100mL)
- dry with materialdried over sodium sulphate
- customThe crude product obtained upon evaporation of the solvent
- customwas further purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-c149b7e51eb84d4c872955058ddfdce3
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846721B2
Linked notes
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