N,N-Dimethylglycine → HCID 57470854, compound

HRID 492875Notes

Reaction equation

HRID 492875 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

After adding N,N-dimethylglycine (2.97 g), 1-hydroxybenzotriazole (3.89 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.27 g) to a solution of 4-(tert-butoxycarbonylamino)piperidine (5.0 g) in N,N-dimethylformamide (70 ml), the mixture was stirred for 46 hours at room temperature under a nitrogen atmosphere. Ethyl acetate (400 ml), brine (200 ml) and 1N aqueous sodium hydroxide (50 ml) were added to the reaction mixture and stirred therewith at room temperature for 30 minutes, and then the mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layers were combined and then washed with 1N aqueous sodium hydroxide and brine in that order and then dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure to provide the title compound (8.03 g, quantitative) as colorless crystals.

Workup

  1. stirringstirred
  2. waitat room temperature for 30 minutes
  3. customthe mixture was partitioned
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with 1N aqueous sodium hydroxide and brine in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe dried organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5deb705aef4a410ca3a59da750b8cade
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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