Triethylamine → HCID 13912802, compound

HRID 652493Notes

Reaction equation

HRID 652493 reaction equation
[C:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]C(O)=O)=[C:6]([CH2:19][CH2:20][CH3:21])[C:5]=1[OH:22])(=[O:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[N:47]1[CH:52]=[CH:51][CH:50]=[C:49]([CH2:53][CH2:54][CH2:55][CH2:56][NH2:57])[CH:48]=1>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:42][C:45]([NH:57][CH2:56][CH2:55][CH2:54][CH2:53][C:49]2[CH:48]=[N:47][CH:52]=[CH:51][CH:50]=2)=[O:30])=[C:6]([CH2:19][CH2:20][CH3:21])[C:5]=1[OH:22])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 72927Pyridine, 3-(4-aminobutyl)-HCID 199401P,P-Diphenylphosphinic azideHCID 137538736-(4-Acetyl-3-hydroxy-2-propylphenoxy)hexanoic acid

Product 1

HCID 13912802HCID 13912802, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a cooled (3) solution of 2.0 g of 6-(4-acetyl-3-hydroxy-2-propylphenoxy)hexanoic acid in 40 mL of anhydrous toluene was added 1.68 mL of diphenylphosphoryl azide followed by 1.36 mL of triethyl amine. The mixture was stirred at 3° for 90 minutes and at 90° for 5 hours. After cooling, 1.07 g of 3-pyridine butanamine was added and heating at 90° was continued for 24 hours. The solvent was removed in vacuo and the residual oil was dissolved in methylene chloride and washed with sodium bicarbonate solution. The dried (over magnesium sulfate) extract was concentrated and purified by HPLC using 7% methanol-ethyl acetate. Crystallization of the combined pure fractions from ethyl acetate-hexane gave 2.0 g, mp 73°-76° (66% yield) of N-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)-pentyl]-N'-[4-(3-pyridinyl)-butyl]urea

Workup

  1. temperatureAfter cooling
  2. temperatureheating at 90°
  3. waitwas continued for 24 hours
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residual oil was dissolved in methylene chloride
  6. washwashed with sodium bicarbonate solution
  7. dry with materialThe dried (over magnesium sulfate)
  8. extractionextract
  9. concentrationwas concentrated
  10. custompurified by HPLC
  11. customCrystallization of the combined pure fractions from ethyl acetate-hexane

Sources & evidence

ORD record
ord-411140fa90a041a4b55cb83bd7356b35
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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