6-Aminohexanoic Acid → N,N'-Dicyclohexylurea

HRID 2210622Notes

Reaction equation

HRID 2210622 reaction equation
NCCCCCC(O)=[O:8].[CH:10]1([N:16]=[C:17]=[N:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CN(C)C=O>[CH:19]1([NH:18][C:17]([NH:16][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)=[O:8])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 5646-Aminohexanoic Acid2×HCID 10868Dicyclohexylcarbodiimide2×

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The 18 atom homobifunctional linker was then synthesized from 5.0 g disuccinimidyl ester intermediate dissolved in 150 ml dry dimethylformamide, 4.20 g 6-aminocaproic acid and 6.93 g dicyclohexylcarbodiimide. The 6-aminocaproic acid was added to the dimethylformamide solution, and the resulting reaction mixture was stirred under a nitrogen blanket for three hours at room temperature of about 22°. The dicyclohexylcarbodiimide was then added, and the reaction mixture was stirred under a nitrogen blanket for about 16 hours at room temperature. Dicyclohexyl urea precipitate which had formed was then separated from the reaction mixture by filtration, and dimethylformamide was evaporated from the filtrate under reduced pressure. Trituration with ether followed by drying under high vacuum yielded 7.94 g 18 atom homobifunctional linker.

Workup

  1. customthe resulting reaction mixture
  2. stirringthe reaction mixture was stirred under a nitrogen blanket for about 16 hours at room temperature

Sources & evidence

ORD record
ord-95f699029a204fdba452d9fdadeb052c
Source dataset
uspto-grants-1995_10
Patent number
US05459242

Reaction notes

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