Dimethylformamide → HCID 66652869, compound

HRID 572548Notes

Reaction equation

[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Br[CH:15]([CH3:20])[C:16]([O:18][CH3:19])=[O:17].[CH3:21]CO[C:24]([CH3:26])=O.C[N:28]([CH:30]=O)C>>[C:1]([C:2]1[CH:7]=[CH:6][C:5]([C@@H:24]([NH:28][C@H:15]([C:16]([O:18][CH3:19])=[O:17])[CH3:20])[CH3:26])=[CH:4][CH:3]=1)#[N:8].[C:1]([C:2]1[CH:7]=[CH:6][C:5]([C@@H:30]([NH:28][C@@H:15]([C:16]([O:18][CH3:19])=[O:17])[CH3:20])[CH3:21])=[CH:4][CH:3]=1)#[N:8]

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 7505Benzonitrile

HCID 8857Ethyl Acetate

HCID 95576Methyl 2-bromopropionate

HCID 516892Sodium Bicarbonate

Product 2

HCID 66652869HCID 66652869, compound

HCID 66652882HCID 66652882, compound

Conditions

Temperature: 75 °C

Procedure

To 4-[(1S)-1-aminoethyl)]benzonitrile (Haoyuan Chemexpress, 1 g; 6.8 mmol) in DMF (15 mL) was added sodium bicarbonate (1.2 g; 14 mmol) and methyl 2-bromopropionate (0.84 mL; 7.5 mmol). The reaction mixture was stirred at 75° C. overnight. EtOAc was added and the organic phase was washed with three times with H2O and once with brine, organic layer was then dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography (EtOAc/Heptane gradient from 5:95 to 25:75), affording methyl N-[(1S)-1-(4-cyanophenyl)ethyl]-L-alaninate (first eluting compound) as a pale yellow solid (480 mg; 30%) and methyl N-[(1S)-1-(4-cyanophenyl)ethyl]-D-alaninate (second eluting compound) as a yellow solid (470 mg; 30%).

Workup

washthe organic phase was washed with three times with H2O and once with brine, organic layer
dry with materialwas then dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash chromatography (EtOAc/Heptane gradient from 5:95 to 25:75)

Sources & evidence

ORD record: ord-528352c73e38482186b0813515406f15
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029405B2

Reaction notes

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