Docosanoic Acid → HCID 22013734, compound

HRID 1532696Notes

Reaction equation

HRID 1532696 reaction equation
C(N(CC)CC)C.[C:8](O)(=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(Cl)(=O)OCC.[NH2:38][C:39]1[CH:40]=[C:41]([CH:47]=[CH:48][C:49]=1[NH:50][CH2:51][CH2:52][N:53]([CH3:55])[CH3:54])[C:42]([N:44]([CH3:46])[CH3:45])=[O:43]>C(Cl)(Cl)Cl>[CH3:54][N:53]([CH3:55])[CH2:52][CH2:51][N:50]1[C:49]2[CH:48]=[CH:47][C:41]([C:42]([N:44]([CH3:46])[CH3:45])=[O:43])=[CH:40][C:39]=2[N:38]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 8215Docosanoic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22013746HCID 22013746, compound

Product 1

HCID 22013734HCID 22013734, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

Triethylamine (1.52 ml) was added to a suspension containing n-docosanoic acid (3.339 g) in chloroform (34 ml), and then ethyl chlorocarbonate (1.04 ml) was added thereto while being cooled with ice. The reaction mixture was stirred for 1.5 hours, and then a solution containing 3-amino-4-{[2-(dimethylarnino)ethyl]amino}-N,N-dimethylbenzamide (2.454 g) in chloroform (12 ml) was added thereto. After being stirred for 3 hours while being cooled with ice, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (8.2 ml) was added to a suspension containing the residue (6.094 g) in ethanol (61 ml). After being stirred for 1.5 hours at 90° C., the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with 1N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (5.119 g) was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=50:1-30:1), thereby yielding the entitled compound (3.320 g) as white solid.

Workup

  1. temperaturewhile being cooled with ice
  2. additionwas added
  3. stirringAfter being stirred for 3 hours
  4. temperaturewhile being cooled with ice
  5. washwashed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  6. dry with materialdried over sodium sulfate anhydride
  7. concentrationconcentrated
  8. additionConcentrated hydrochloric acid (8.2 ml) was added to a suspension
  9. additioncontaining the residue (6.094 g) in ethanol (61 ml)
  10. stirringAfter being stirred for 1.5 hours at 90° C.
  11. concentrationthe reaction mixture was concentrated
  12. additionThe residue, with ethyl acetate added
  13. washwas washed with 1N sodium hydroxide aqueous solution and saturated brine successively
  14. dry with materialdried over sodium sulfate anhydride
  15. concentrationconcentrated
  16. customThe residue (5.119 g) was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=50:1-30:1)

Sources & evidence

ORD record
ord-59e0efafa9134bc593512a74d9b03a99
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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