Triethylamine → HCID 178520458, compound

HRID 37302Notes

Reaction equation

HRID 37302 reaction equation
[CH2:1]1[C:6](=[O:7])[S: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])[S: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 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27291133-Cyclododecylpropanoic acidHCID 10214383Thiotetronic acid

Product 1

HCID 178520458HCID 178520458, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 0.80 g of thiotetronic 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-ethyl carbodiimide 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 1N hydrochloric acid and extracted 3 times with ethyl acetate. The organic layers are combined, washed with brine, filtered and evaporated to give a brown oil. The oil is subjected to flash chromatography using acidic silica gel and hexane/ethyl acetate (9:1) as the mobile phase to give an off white solid: m.p. 60°-62° C.; IR (KBr) 2940, 1700, 1630, and 1590 cm1 : NMR (CDCl3) δ 1.33 (bs, 22H), 1.49 (bs, 1H), 1.58 (m, 2H), 2.96 (m, 2H), 3.77 and 3.98 (singlets, 2H); MS (EI) M+338.

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 1N hydrochloric acid
  4. extractionextracted 3 times with ethyl acetate
  5. washwashed with brine
  6. filtrationfiltered
  7. customevaporated
  8. customto give a brown oil
  9. customto give an off white solid

Sources & evidence

ORD record
ord-8ac26025b81d4095869c156cdcd07859
Source dataset
uspto-grants-1995_05
Patent number
US05420153

Reaction notes

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