Triethylamine → 4-Hydroxy-2-oxo-2,5-dihydro-furan-3-carboxylic acid 2-cyclododecyl-ethylamide

HRID 37310Notes

Reaction equation

HRID 37310 reaction equation
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.[CH:15]1([CH2:27][CH2:28][N:29]=[C:30]=[O:31])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[K+].[Br-]>C(Cl)(Cl)Cl>[CH:15]1([CH2:27][CH2:28][NH:29][C:30]([C:1]2[C:6](=[O:7])[O:5][CH2:4][C:2]=2[OH:3])=[O:31])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 253877Potassium BromideHCID 521261Tetronic acidHCID 193718152-Cyclododecylethyl isocyanate

Product 1

HCID 546991564-Hydroxy-2-oxo-2,5-dihydro-furan-3-carboxylic acid 2-cyclododecyl-ethylamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a dry flask containing 40 mL of chloroform was added 1.87 g (18.7 mmol) of tetronic acid, 2.29 g (18.7 mmol) of 4-N,N-dimethylaminopyridine, 2.6 mL (18.7 mmol) of triethylamine followed by 4.4 g (18.7 mmol) of 2-cyclododecylethyl isocyanate. The reaction mixture was allowed to stir overnight at room temperature, after which time a small amount of starting materials was still evident by TLC. The reaction mixture was quenched with 1N HCl, the layers separated, the organic fraction dried over MgSO4, filtered, and stripped of solvent. The residue was flash chromatographed using acidic silica gel eluting with 25% EtOAc/hexane to give a yellow solid. M.P. 135°-137° C. Spectral data follow: 1H NMR (DMSO-d6) δ 8.05 (bs, 1H), 4.6 (s, 2H), 4.2 (bs, 10H), 3.25 (t, 2H), 2.5 (s, 3H), 1.2-1.4 (bm, >20H); IR (KBr) 3340, 2920, 2850 (C--H), 1750, 1650 cm-1 (C=0);

Workup

  1. customThe reaction mixture was quenched with 1N HCl
  2. customthe layers separated
  3. dry with materialthe organic fraction dried over MgSO4
  4. filtrationfiltered
  5. customchromatographed
  6. customto give a yellow solid

Sources & evidence

ORD record
ord-c7bedd84b32442cfa1e54c07cd4c8dd1
Source dataset
uspto-grants-1995_05
Patent number
US05420153

Reaction notes

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