Ethanolamine → HCID 15949136, compound

HRID 910887Notes

Reaction equation

HRID 910887 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=O)[CH:9]=[CH:10][CH:11]=1.ON1C2C=CC=CC=2N=N1.[CH2:31]([CH2:33][NH2:34])[OH:32].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C=O)C>[OH:32][CH2:31][CH2:33][NH:34][C:13](=[O:15])[CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]2[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:2]=2[CH3:1])[CH:7]=1

Participants

7

Reactant 4

HCID 700EthanolamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 9838311HCID 9838311, compound

Product 1

HCID 15949136HCID 15949136, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(2,6-Dimethylbenzyloxy)phenylacetic acid (Step C, 6.0 g, 22.2 mmol), 1-Hydroxybenzotriazole (7.19 g, 53.2 mmol), and Ethanolamine (2.70 g, 44.2 mmol) in methylene chloride (30 ml) and DMF (5 ml) was added EDCI (7.66 g, 40 mmol) at 0° C., the resulting reaction mixture was stirred at room temperature for 24 hours and concentrated under reduced pressure. The residue was dissolved in methylene chloride (10 ml) and washed with NaHCO3, 0.1M HCl, brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol, 9:1) to provide the title compound.

Workup

  1. customthe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride (10 ml)
  4. washwashed with NaHCO3, 0.1M HCl, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on a silica gel column (chloroform:methanol, 9:1)

Sources & evidence

ORD record
ord-5a5b6b0a6caf4cfb9815bed037ee8f4f
Source dataset
uspto-grants-2011_09
Patent number
US08022249B2

Reaction notes

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