Ethanolamine → 7-beta-D-galactopyranosyloxycoumarin-4-acetic acid-(2-hydroxyethyl)amide

HRID 610661Notes

Reaction equation

HRID 610661 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([CH2:36][C:37]([O-])=[O:38])=[CH:30][C:31](=[O:35])[O:32]2)=[CH:27][CH:26]=1)(=O)C.[CH2:40]([CH2:42][NH2:43])[OH:41]>C(Cl)Cl.CO.CCOCC>[OH:41][CH2:40][CH2:42][NH:43][C:37](=[O:38])[CH2:36][C:29]1[C:28]2[C:33](=[CH:34][C:25]([O:24][C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])=[CH:26][CH:27]=2)[O:32][C:31](=[O:35])[CH:30]=1

Participants

6

Reactant 2

HCID 700EthanolamineHCID 86754922HCID 86754922, compound2×

Product 1

HCID 99541407-beta-D-galactopyranosyloxycoumarin-4-acetic acid-(2-hydroxyethyl)amideYield 37.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

43 g (0.076 moles) of 7-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)coumarin-4-acetate (i.e. compound 1 prepared as described in Scheme 1) was dissolved in 430 ml of methylene chloride in a 1 liter RB flask. 43 ml (0.712 moles) of ethanolamine was dissolved in 43 ml of methanol and added to the above solution. The solution was stirred at room temperature for 60 hrs and the resulting solid residue was filtered and washed with 50 ml of methylene chloride. The solid was suspended in 250 ml of methanol and stored in the freezer for 12 hrs. The solid was filtered again and suspended in 700 ml of methanol and refluxed for 30 min. The cloudy suspension was cooled to room temperature, then further cooled in an ice bath and filtered. The wet solid thus obtained was suspended in 200 ml of ether and stirred for 30 min., then filtered and vacuum dried at room temperature to give 12 g of an off-white solid. The yield was 37%. The structure was confirmed by 1H NMR and MS (as in Example 1).

Workup

  1. additionadded to the above solution
  2. filtrationthe resulting solid residue was filtered
  3. washwashed with 50 ml of methylene chloride
  4. waitstored in the freezer for 12 hrs
  5. filtrationThe solid was filtered again
  6. temperaturerefluxed for 30 min
  7. temperatureThe cloudy suspension was cooled to room temperature
  8. temperaturefurther cooled in an ice bath
  9. filtrationfiltered
  10. customThe wet solid thus obtained
  11. stirringstirred for 30 min.
  12. filtrationfiltered
  13. customvacuum dried at room temperature

Sources & evidence

ORD record
ord-81773609d59c4a23bdcf5304d2876e25
Source dataset
uspto-grants-1999_12
Patent number
US05998593

Reaction notes

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