Triethylamine → HCID 54466140, compound

HRID 2392602Notes

Reaction equation

HRID 2392602 reaction equation
C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O.[C:14]([NH:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][CH:37]=1)(=[O:34])[CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH:21]=[CH:22][CH2:23][CH:24]=[CH:25][CH2:26][CH:27]=[CH:28][CH2:29][CH:30]=[CH:31][CH2:32][CH3:33].CCN(CC)CC.[CH:51]([C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([CH:60]([CH3:62])[CH3:61])[C:55]=1[N:63]=[C:64]=[O:65])([CH3:53])[CH3:52]>C1COCC1>[C:14]([NH:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH:41][C:64]([NH:63][C:55]2[C:54]([CH:51]([CH3:52])[CH3:53])=[CH:59][CH:58]=[CH:57][C:56]=2[CH:60]([CH3:62])[CH3:61])=[O:65])=[CH:38][CH:37]=1)(=[O:34])[CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH:21]=[CH:22][CH2:23][CH:24]=[CH:25][CH2:26][CH:27]=[CH:28][CH2:29][CH:30]=[CH:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10236NinhydrinHCID 922592,6-Diisopropylphenyl isocyanateHCID 53978276HCID 53978276, compound

Product 1

HCID 54466140HCID 54466140, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was subjected to TLC analysis [silica gel plate, developing solvent:CHCl3 -MeOH-H2O (90:10:1)]. As a result, a single spot was obtained by the detection with iodine and a 0.2% ninhydrin reagent. The obtained 4-(N-5,8,11,14,17-eicosapentaenoylamino)benzylamine (813 mg, 2 mmol) and Et3N (204 mg, 2 mmol) were dissolved in anhydrous THF (10 ml), and 2,6-diisopropylphenyl isocyanate (406 mg, 2 mmol) was added. The mixture was reacted for about 2 hours under cooling in a nitrogen stream, and concentrated under reduced pressure. The obtained concentrate was dissolved in a small amount of CHCl3 and applied to an SiO2 (800 g) column activated with CHCl3 in advance, which was followed by elution with CHCl3 (600 ml) and CHCl3 -MeOH (98:2, 800 ml) in this order. The objective fractions were recovered from the obtained eluate fractions based on TLC analysis as an index, and concentrated to give the objective compound (1.07 g, yield 88%).

Workup

  1. customThe mixture was reacted for about 2 hours
  2. temperatureunder cooling in a nitrogen stream
  3. concentrationconcentrated under reduced pressure
  4. concentrationThe obtained concentrate
  5. dissolutionwas dissolved in a small amount of CHCl3
  6. washwas followed by elution with CHCl3 (600 ml) and CHCl3 -MeOH (98:2, 800 ml) in this order
  7. customThe objective fractions were recovered from the obtained eluate fractions
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b2683f67373542e98c3942b8ed100aba
Source dataset
uspto-grants-1998_09
Patent number
US05801178

Reaction notes

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