Dimethylformamide → HCID 66652820, compound

HRID 572547Notes

Reaction equation

HRID 572547 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

7

Reactant 5

HCID 6228DimethylformamideHCID 7505BenzonitrileHCID 8857Ethyl AcetateHCID 95576Methyl 2-bromopropionateHCID 516892Sodium Bicarbonate

Product 2

HCID 66652820HCID 66652820, compoundYield 43%HCID 66652962HCID 66652962, compoundYield 40%

Conditions

Temperature
75 °C

Procedure

To 4-[(1R)1-aminoethyl)]benzonitrile (Haoyuan Chemexpress, 3.4 g; 23 mmol) in DMF (34 mL) was added sodium bicarbonate (3.9 g; 46 mmol) and methyl 2-bromopropionate (2.8 mL; 25 mmol). The reaction mixture was stirred at 75° C. overnight. EtOAc was added to the reaction mixture and the organic phase was washed 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-[(1R)-1-(4-cyanophenyl)ethyl]-D-alaninate (first eluting compound) as a white solid (2.1 g, 40%) and methyl N-[(1R)-1-(4-cyanophenyl)ethyl]-L-alaninate (second eluting compound) as an orange solid (2.3 g, 43%).

Workup

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

Sources & evidence

ORD record
ord-466ef1f703f3470983d30c8508c23129
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

Loading…