Dicyclohexylcarbodiimide → HCID 131731312, compound

HRID 2364936Notes

Reaction equation

HRID 2364936 reaction equation
[CH3:1][N:2]([CH3:9])[CH:3]([CH3:8])[CH2:4][C:5]([OH:7])=[O:6].O[N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17].C1(N=C=NC2CCCCC2)CCCCC1.O.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(Cl)Cl.C(#N)C>[S:40]([C:37]1[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=1)([OH:43])(=[O:42])=[O:41].[O:17]=[C:12]1[CH2:13][CH2:14][C:15](=[O:16])[N:11]1[O:6][C:5](=[O:7])[CH2:4][CH:3]([N:2]([CH3:9])[CH3:1])[CH3:8]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 21935982Butanoic acid, 3-(dimethylamino)- (9CI)

Product 1

HCID 131731312HCID 131731312, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

6.55 g (50 mMol) 3-dimethylamino-butyric acid 20 was added to 5.75 g (50 mMol) N-hydroxysuccinimide and 11.05 g (55 mMol) dicyclohexyl carbodiimide in 100 ml CH2Cl2. The reaction mixture was stirred for 16 h at RT. The obtained urea was filtrated and the solution was evaporated. The residue, dissolved in 10 ml acetonitrile, was added under stirring to a solution of 9.51 g (50 mMol) 4-toluenesulfonic acid monohydrate in acetonitrile (30 ml). The solvent was evaporated under vacuum and the product was recrystallized from acetonitrile or acetone.

Workup

  1. filtrationThe obtained urea was filtrated
  2. customthe solution was evaporated
  3. dissolutionThe residue, dissolved in 10 ml acetonitrile
  4. additionwas added
  5. customThe solvent was evaporated under vacuum
  6. customthe product was recrystallized from acetonitrile or acetone

Sources & evidence

ORD record
ord-c7059a9b925344ac8b10595ff68b7bbf
Source dataset
uspto-grants-2014_04
Patent number
US08697604B2

Reaction notes

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