Ethanolamine → HCID 86653773, compound

HRID 1021200Notes

Reaction equation

HRID 1021200 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:32]([CH2:34][NH2:35])[OH:33]>C1COCC1>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15][CH2:16][C:17]([NH:35][CH2:34][CH2:32][OH:33])=[O:19]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 682631,1'-CarbonyldiimidazoleHCID 86653774HCID 86653774, compound

Product 1

HCID 86653773HCID 86653773, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 25 mL THF was dissolved 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-butanoic acid (1.32 g, 4.96 mmol) prepared as described in Example 1. CDI (884 mg, 5.46 mmol, 1.1 equiv.) was added and the solution stirred for 1.75 h at room temperature. A small portion (2 mL) was removed for other studies. The remainder was treated with 370 μL ethanolamine (365 mg, 5.96 mmol, 1.3 equiv.) and let stir at room temperature overnight. The clear pale brown solution was concentrated and the residue dissolved into 100 mL isopropyl acetate and washed with 100 mL 1.25 M HCl, 1×100 mL saturated aqueous NaCl, 1×50 mL brine and dried over Na2SO4. The reaction mixture was concentrated yielding 1.15 g of a white powder. M++H at 310 m/z;

Workup

  1. customprepared
  2. customA small portion (2 mL) was removed for other studies
  3. stirringlet stir at room temperature overnight
  4. concentrationThe clear pale brown solution was concentrated
  5. dissolutionthe residue dissolved into 100 mL isopropyl acetate
  6. washwashed with 100 mL 1.25 M HCl, 1×100 mL saturated aqueous NaCl, 1×50 mL brine
  7. dry with materialdried over Na2SO4
  8. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-7c7f88d70c1c4697ad46e7ac6784a483
Source dataset
uspto-grants-2014_05
Patent number
US08716527B2

Reaction notes

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