N,N-Dimethylglycine → HCID 11816481, compound

HRID 2364934Notes

Reaction equation

HRID 2364934 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([OH:7])=[O:6])[CH3:3].O[N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[O:15]=[C:10]1[CH2:11][CH2:12][C:13](=[O:14])[N:9]1[O:6][C:5](=[O:7])[CH2:4][N:2]([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 673N,N-DimethylglycineHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 11816481HCID 11816481, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.15 g (50 mMol) Dimethylamino-acetic acid 15 was added to 5.75 g (50 mMol) N-hydroxy-succinimide and 11.05 g (55 mMol) dicyclohexyl-carbodiimide in 100 ml CH2Cl2 at 0° C. The reaction mixture was stirred for 20 h at RT. The residue was filtered and the filtrate was evaporated in vacuum to dryness. The residue was then dissolved in diethylether, mixed with A-Kohle. The solution was filtered off and evaporated. The obtained oil was dissolved in a small amount of diethylether to get a crystallization of the product. The cooled crystal solution was filtered off. The crystals were once again dissolved in Diethylether, treated with A-Kohle and the solution was filtered off. Those purification steps were repeated several times until the obtaining of a pure product in 1H-NMR

Workup

  1. filtrationThe residue was filtered
  2. customthe filtrate was evaporated in vacuum to dryness
  3. dissolutionThe residue was then dissolved in diethylether
  4. additionmixed with A-Kohle
  5. filtrationThe solution was filtered off
  6. customevaporated
  7. dissolutionThe obtained oil was dissolved in a small amount of diethylether
  8. customto get
  9. customa crystallization of the product
  10. filtrationThe cooled crystal solution was filtered off
  11. dissolutionThe crystals were once again dissolved in Diethylether
  12. additiontreated with A-Kohle and the solution
  13. filtrationwas filtered off
  14. customThose purification steps
  15. customobtaining of a pure product in 1H-NMR

Sources & evidence

ORD record
ord-fedfbf920ef74206b5d156ddcbee1d10
Source dataset
uspto-grants-2014_04
Patent number
US08697604B2

Reaction notes

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