Tetrahydrofuran → N,N'-Dicyclohexylurea

HRID 1600576Notes

Reaction equation

HRID 1600576 reaction equation
C1C[O:4]CC1.[CH2:6]1[CH2:11][CH2:10][CH:9]([N:12]=[C:13]=[N:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:8][CH2:7]1.C(N)CCCCCCCCCCC>N1C=CC=CC=1>[C:13]([NH:12][CH:9]1[CH2:8][CH2:7][CH2:6][CH2:11][CH2:10]1)([NH:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:4]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 10868Dicyclohexylcarbodiimide2×HCID 13583Dodecylamine

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Procedure

If the desacylsaponins are soluble in anhydrous pyridine, alone or with anhydrous THF, the reaction can be carried out with DCC. 100 mg of (4) (60 μmoles) are dissolved in pyridine and/or THF, using no less than 1 ml but no more than 5 ml. 1 ml of a 0.3M dodecylamine solution (300 μmoles) in pyridine and/or THF is thereafter added to the reaction mixture, followed by 300 μmoles of dry DCC. The mixture is allowed to react with mixing overnight at 0° C. to 10° C. During the reaction, insoluble dicyclohexylurea is formed; this is removed by centrifugation. The supernatant containing the conjugated desacylsaponins (5) is diluted with 10 volumes of EtOAc to precipitate (5). The EtOAc containing the free alkyl amine, residual DCC, and the pyridine and/or THF is discarded. Precipitate is washed with EtOAc, dissolved in water and re-extracted with EtOAc before removing the EtOAc and lyophilizing.

Workup

  1. customto react
  2. additionwith mixing overnight at 0° C. to 10° C
  3. customDuring the reaction

Sources & evidence

ORD record
ord-810fbff159014a929773c8ef265e98d1
Source dataset
uspto-grants-1999_11
Patent number
US05977081

Reaction notes

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