6-Aminohexanoic Acid → N,N'-Dicyclohexylurea

HRID 483770Notes

Reaction equation

HRID 483770 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](=[O:8])[NH:16][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[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-cec33d95889b49ddb38a7992d47d7c66
Source dataset
uspto-grants-1993_07
Patent number
US05227311

Reaction notes

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