N,N-Dimethylglycine → HCID 54321913, compound

HRID 1804709Notes

Reaction equation

HRID 1804709 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[CH3:16][N:17]([CH3:22])[CH2:18][C:19](O)=[O:20].Cl.C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:16][N:17]([CH3:22])[CH2:18][C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:6][CH:7]=1)=[O:20]

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 516892Sodium BicarbonateHCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 54321913HCID 54321913, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A 100 mL round bottom flask with stirbar was charged with tert-butyl 4-aminophenylcarbamate (2.38 g, 11.43 mmol), 2-(dimethylamino)acetic acid (1.25 g, 12.12 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (2.59 g, 13.51 mmol) and 4-dimethylaminopyridine (0.05 g, 0.409 mmol) in dichloromethane (50 ml). The solution was stirred at ambient temperature for 2 hours. The mixture was shaken in a separatory funnel with 50 mL aqueous sodium bicarbonate, and the organics were separated and dried over magnesium sulfate and filtered. Solvent removal gave the title compound. MS (ESI(+)) m/e 294.0 (M+H)+.

Workup

  1. customthe organics were separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customSolvent removal

Sources & evidence

ORD record
ord-dc953b93137a4a8ca9810b06e7acc7ee
Source dataset
uspto-grants-2013_01
Patent number
US08354422B2

Reaction notes

Loading…