N,N-Dimethylglycine → HCID 24768017, compound

HRID 556259Notes

Reaction equation

HRID 556259 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19]([NH2:20])=[N:18][C:16]2=[O:17])[C@H:12]([OH:23])[C@:11]1([C:25]#[CH:26])[OH:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:27][N:28]([CH3:33])[CH2:29][C:30](O)=[O:31].Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19]([NH:20][C:30](=[O:31])[CH2:29][N:28]([CH3:33])[CH3:27])=[N:18][C:16]2=[O:17])[C@H:12]([OH:23])[C@:11]1([C:25]#[CH:26])[OH:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 673N,N-DimethylglycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 24767999HCID 24767999, compound

Product 1

HCID 24768017HCID 24768017, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Compound 1 (1.9 g, 5 mmol), N,N-dimethylglycine (1.0 g, 10 mmol), N,N-dimethylaminopyridine (0.1 g, 0.8 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.9 g, 10 mmol) were added to DMF (20 mL) under ice-cooling, and the mixture was stirred for one day at 40° C. The reaction mixture was concentrated, and ethyl acetate was added to the residue. The organic layer was washed with saturated aqueous sodium hydrogen carbonate (50 mL) and saturated brine (50 mL), and then dried over magnesium sulfate. Magnesium sulfate was removed through filtration, and the filtrate was concentrated. The residue was purified through silica gel chromatography (4% methanol/chloroform solvent mixture). The eluate was concentrated, and the residue was recrystallized from hexane, to thereby yield Compound 17 (0.46 g, 20%).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additionethyl acetate was added to the residue
  4. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (50 mL) and saturated brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. customMagnesium sulfate was removed through filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified through silica gel chromatography (4% methanol/chloroform solvent mixture)
  9. concentrationThe eluate was concentrated
  10. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-bf85a3eaa49a4207b1fad3e45decb496
Source dataset
uspto-grants-2011_11
Patent number
US08058261B2

Reaction notes

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