Dicyclohexylcarbodiimide → HCID 11253866, compound

HRID 2364930Notes

Reaction equation

HRID 2364930 reaction equation
Cl.[CH:2]([N:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]([CH3:8])[CH3:7])([CH3:4])[CH3:3].O[N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20].C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[O:20]=[C:15]1[CH2:16][CH2:17][C:18](=[O:19])[N:14]1[O:11][C:10](=[O:12])[CH2:9][N:5]([CH:6]([CH3:7])[CH3:8])[CH:2]([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 46735981Diisopropylamino-acetic acid hydrochloride

Product 1

HCID 11253866HCID 11253866, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.82 g (19.5 mMol) diisopropylamino-acetic acid hydrochloride (3), in 50 ml DMF, was added to 2.24 g (19.5 mMol) N-hydroxysuccinimide and 8.04 g (39 nMol) dicyclohexylcarbodiimide. The reaction mixture was stirred for 16 h at RT. The residue was filtered and the filtrate was evaporated in vacuum to dryness. After dissolving the residue in CH2Cl2, the solution was washed with NaHCO3, dried (sodium sulphate) and the solvent evaporated. The compound was then recrystallised from diisopropylether.

Workup

  1. filtrationThe residue was filtered
  2. customthe filtrate was evaporated in vacuum to dryness
  3. dissolutionAfter dissolving the residue in CH2Cl2
  4. washthe solution was washed with NaHCO3
  5. dry with materialdried (sodium sulphate)
  6. customthe solvent evaporated
  7. customThe compound was then recrystallised from diisopropylether

Sources & evidence

ORD record
ord-e82303fbef3d496fbcc8564df4c013f7
Source dataset
uspto-grants-2014_04
Patent number
US08697604B2

Reaction notes

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