Dimethylamine → HCID 86678841, compound

HRID 1620679Notes

Reaction equation

HRID 1620679 reaction equation
[C:1]([NH:11][C@H:12]([C:15]([OH:17])=O)[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:18][NH:19][CH3:20]>C(O)C>[CH2:4]([O:3][C:1](=[O:2])[NH:11][C@@H:12]([CH2:13][OH:14])[C:15]([N:19]([CH3:20])[CH3:18])=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 100310N-(Benzyloxycarbonyl)-L-serine

Product 1

HCID 86678841HCID 86678841, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-carbobenzoxy-L-serine (5.00 g) in ethanol (70 mL) were added dimethylamine (2.51 mL) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride n-hydrate (6.23 g), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate/tetrahydrofuran and water. The organic layer was separated, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (3.23 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate/tetrahydrofuran
  3. customThe organic layer was separated
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8d8c2e6337c54c449ca16f76c9efc725
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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