Bromoacetonitrile → (R)-cyanomethyl 2-((tert-butoxycarbonyl)amino)-3-(tert-butyldisulfanyl)propanoate
Reaction equation
Br[CH2:2][C:3]#[N:4].C(N(C(C)C)C(C)C)C.[C:14]([O:18][C:19]([NH:21][C@@H:22]([CH2:26][S:27][S:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:23]([OH:25])=[O:24])=[O:20])([CH3:17])([CH3:16])[CH3:15].[Cl-].[NH4+]>CN(C=O)C>[C:14]([O:18][C:19]([NH:21][C@@H:22]([CH2:26][S:27][S:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:23]([O:25][CH2:2][C:3]#[N:4])=[O:24])=[O:20])([CH3:17])([CH3:16])[CH3:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Bromoacetonitrile (0.473 ml, 6.78 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.444 ml, 2.49 mmol) were added to a solution of (R)-2-((tert-butoxycarbonyl)amino)-3-(tert-butyldisulfanyl)propanoic acid (Compound 2k-A) (700 mg, 2.26 mmol) in DMF (5 ml), and the mixture was stirred at room temperature for 10 minutes. A saturated aqueous ammonium chloride solution (1 ml) was added to the reaction mixture, after which the mixture was extracted with ethyl acetate and the organic layer was washed with water. The organic extract was then dried over magnesium sulfate. Following concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→70/30) to afford (R)-cyanomethyl 2-((tert-butoxycarbonyl)amino)-3-(tert-butyldisulfanyl)propanoate (Compound 21-A) (748 mg, 95%).
Workup
- extractionafter which the mixture was extracted with ethyl acetate
- washthe organic layer was washed with water
- extractionThe organic extract
- dry with materialwas then dried over magnesium sulfate
- concentrationconcentration under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→70/30)
Sources & evidence
- ORD record
- ord-e54d10dc99e2401ebfb986abb36d9c9e
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
Loading…