Acetylethanolamine → HCID 178474919, compound

HRID 2082325Notes

Reaction equation

HRID 2082325 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]1([CH2:22][CH2:23][CH2:24][PH:25](=[O:27])[OH:26])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:28]([NH:31][CH2:32][CH2:33]O)(=[O:30])[CH3:29]>O1CCCC1.CN(C)C1C=CN=CC=1>[C:16]1([CH2:22][CH2:23][CH2:24][PH:25](=[O:26])[O:27][CH2:33][CH2:32][NH:31][C:28](=[O:30])[CH3:29])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8880AcetylethanolamineHCID 10868DicyclohexylcarbodiimideHCID 178527054HCID 178527054, compound

Product 1

HCID 178474919HCID 178474919, compoundYield 29.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.31 g (1.5 mmol) of 1,3-dicyclohexylcarbodiimide in tetrahydrofuran (3 ml) is added 0.28 g (1.5 mmol) of 3-phenylpropylphosphinic acid in tetrahydrofuran (1 ml). The resulting suspension is stirred for 10 minutes at room temperature. N-acetyl ethanolamine (0.10 g, 1.0 mol) is then added, followed by 18 mg or 4-dimethylaminopyridine. The mixture is stirred for 2 hours. The solvent is evaporated under reduced pressure, and the residue is stirred with ethyl acetate (20 ml). The resulting suspension is filtered. The filtrate is washed with 5% potassium hydrogen sulfate (8 ml), saturated sodium bicarbonate (2×5 ml), and brine (5 ml), and evaporated to give 0.12 g of a colorless oil.

Workup

  1. stirringThe mixture is stirred for 2 hours
  2. customThe solvent is evaporated under reduced pressure
  3. stirringthe residue is stirred with ethyl acetate (20 ml)
  4. filtrationThe resulting suspension is filtered
  5. washThe filtrate is washed with 5% potassium hydrogen sulfate (8 ml), saturated sodium bicarbonate (2×5 ml), and brine (5 ml)
  6. customevaporated

Sources & evidence

ORD record
ord-e097ebdedb164acfaf46a0b775e3c606
Source dataset
uspto-grants-1993_02
Patent number
US05189023

Reaction notes

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