Ethanolamine → 7-Hydroxycoumarin-4-acetic acid-(2-hydroxyethyl) amide

HRID 610663Notes

Reaction equation

HRID 610663 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:30])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)=[CH:14][CH:15]=2)[O:10][C:9](=[O:29])[CH:8]=1.C(CN)O>CN(C=O)C>[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:30])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[O:10][C:9](=[O:29])[CH:8]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 99541407-beta-D-galactopyranosyloxycoumarin-4-acetic acid-(2-hydroxyethyl)amide

Product 1

HCID 538312567-Hydroxycoumarin-4-acetic acid-(2-hydroxyethyl) amideYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg (0.85 mmole) of 7-hydroxycoumarin-4-methyl ester 2 (prepared as described in Scheme 1) was dissolved in 5 ml of dry DMF and stirred with 0.5 g (8.5 mmoles) of ethanolamine at room temperature for 52 hrs. The DMF was then evaporated from the dark brown solution. The residue obtained after further evaporation with methanol was dissolved in water and purified on a C-8 RP-HPLC column using a gradient of 5/95 CH3CN/water (0.1% TFA) to 30170 CH3CN/water (0.1% TFA) in 25.5 min. The peak eluting at 21.6 min was collected and lyophilized to give 0.16 g of an off-white powder MS: Mol. Formula, C13H13NO5 ; Calculated: 263.26, found (M+H)+ 264.2.

Workup

  1. customThe DMF was then evaporated from the dark brown solution
  2. customThe residue obtained
  3. customafter further evaporation with methanol
  4. dissolutionwas dissolved in water
  5. custompurified on a C-8 RP-HPLC column
  6. customin 25.5 min
  7. washThe peak eluting at 21.6 min
  8. customwas collected

Sources & evidence

ORD record
ord-a7a7e2f60f05430ea93e258c5df0d7aa
Source dataset
uspto-grants-1999_12
Patent number
US05998593

Reaction notes

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