N,N-Dimethylglycine → HCID 57470854, compound

HRID 1712636Notes

Reaction equation

HRID 1712636 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:30]([O:34][C:35]([NH:37][CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[O:36])([CH3:33])([CH3:32])[CH3:31].[OH-].[Na+]>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C>[CH3:1][N:2]([CH3:7])[CH2:3][C:4]([N:41]1[CH2:40][CH2:39][CH:38]([NH:37][C:35](=[O:36])[O:34][C:30]([CH3:32])([CH3:31])[CH3:33])[CH2:43][CH2:42]1)=[O:5]

Participants

9

Reactant 5

HCID 673N,N-DimethylglycineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 7238334-(N-Boc-amino)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57470854HCID 57470854, compoundYield 112.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N,N-Dimethylglycine (2.97 g), 1-hydroxybenzotriazole (3.89 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.27 g) were added to a solution of 4-(tert-butoxycarbonylamino)piperidine (5.0 g) in N,N-dimethylformamide (70 ml), followed by stirring at room temperature under a nitrogen atmosphere for 46 hours. Ethyl acetate (400 ml), brine (200 ml) and a 1N aqueous solution of sodium hydroxide (50 ml) were added to the reaction mixture, followed by stirring at room temperature for 30 minutes, and the mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layer was collected, washed with a 1N aqueous solution of sodium hydroxide and brine in this order, and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure to give the title compound (8.03 g, quant.) as white crystals.

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. customthe mixture was partitioned
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. customThe organic layer was collected
  5. washwashed with a 1N aqueous solution of sodium hydroxide and brine in this order
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe dried organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-877d869909ac4610993447674a780fc9
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

Loading…