Triethylamine → HCID 178520457, compound

HRID 37301Notes

Reaction equation

HRID 37301 reaction equation
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH:24]1([CH2:36][CH2:37][C:38](O)=[O:39])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.Cl.CN(C)CCCN=C=NCC.[K+].[Br-]>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[CH:24]1([CH2:36][CH2:37][C:38]([C:1]2[C:6](=[O:7])[O:5][CH2:4][C:2]=2[OH:3])=[O:39])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 253877Potassium BromideHCID 521261Tetronic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27291133-Cyclododecylpropanoic acid

Product 1

HCID 178520457HCID 178520457, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 0.70 g (7 mmol) of tetronic acid in 20 ml of dry dimethylformamide at 0° C. is added 1.1 ml (836 mg, 8.3 mmol) of triethylamine and 0.31 g (2.5 mmol) of dimethylaminopyridine. After stirring for 5 minutes, 2.0 g (8.3 mmol) of 3-cyclododecylpropanoic acid is added followed by 1.6 g (8.3 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. After 10 minutes the ice bath is removed and the reaction mixture is allowed to stir overnight at room temperature. The reaction mixture is then poured into 1.0N hydrochloric acid and extracted 3 times with ethyl acetate. The organic layers are combined, washed with brine, dried over magnesuim sulfate, filtered and concentrated to give a yellow oil. The oil is subjected to flash chromatography using acidic silica gel and hexane/ethyl acetate (3:2) as the mobile phase to give an off white solid: m.p. 99°-102° C.; IR (KBr) 2940, 1710, 1600 and 1470 cm-1 ; NMR (CDCl3) (mixture of tautomeric forms) δ 1.34 (mc, 22H), 1.50 (bs, 1H), 1.61 (m, 2H), 2.92 (m, 2H), 4.55 and 4.70 (s, 2H); MS (EI)

Workup

  1. customAfter 10 minutes the ice bath is removed
  2. stirringto stir overnight at room temperature
  3. additionThe reaction mixture is then poured into 1.0N hydrochloric acid
  4. extractionextracted 3 times with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over magnesuim sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a yellow oil
  10. customto give an off white solid

Sources & evidence

ORD record
ord-4c0de7bd79f648d6961f6980efdeb6b2
Source dataset
uspto-grants-1995_05
Patent number
US05420153

Reaction notes

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