1,2-Dimethoxyethane → HCID 86667975, compound

HRID 2403616Notes

Reaction equation

HRID 2403616 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][NH:6][C:7](=[O:17])[CH2:8][NH:9][C:10](=O)[O:11]C(C)(C)C.[O:21]1[C:26]2[CH:27]=[CH:28][C:29](B(O)O)=[CH:30][C:25]=2[O:24][CH2:23][CH2:22]1.[C:34](=[O:37])([O-:36])[O-].[Na+].[Na+].[CH3:40][O:41][CH2:42][CH2:43][O:44]C>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:34]([C@@H:10]([C@H:43]([C:42]([OH:41])=[O:21])[OH:44])[OH:11])([OH:36])=[O:37].[O:21]1[C:26]2[CH:27]=[CH:28][C:29]([C:2]3[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=3)[CH2:5][N:6]([CH3:40])[C:7](=[O:17])[CH2:8][NH2:9])=[CH:30][C:25]=2[O:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2776178(2,3-Dihydro-1,4-benzodioxin-6-yl)boronic acidHCID 68152809HCID 68152809, compound

Product 1

HCID 86667975HCID 86667975, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl {2-[(3-bromobenzyl)amino]-2-oxoethyl}carbamate (350 mg) was dissolved in DME (3 ml) and water (1.5 ml), and 1,4-benzodioxane-6-boronic acid (194 mg), sodium carbonate (313 mg), and tetrakis(triphenylphosphine)palladium (34 mg) were added thereto, followed by stirring at 80° C. for 1 day. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH). The product was dissolved in MeOH (3.5 ml), and 4 M hydrogen chloride/EtOAc (2.0 ml) was added thereto, followed by stirring at room temperature for one day. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH). The product was dissolved in EtOH (3 ml), and L-tartaric acid (126 mg) was added thereto, followed by stirring at room temperature for 2 hours. The precipitated solid was collected by filtration to obtain N-[3-(2,3-dihydro-1,4-benzodioxin-6-yl)benzyl]-N-methylglycinamide L-tartrate (453 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogen carbonate solution was added
  3. extractionfollowed by extraction with CHCl3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)
  7. dissolutionThe product was dissolved in MeOH (3.5 ml)
  8. addition4 M hydrogen chloride/EtOAc (2.0 ml) was added
  9. stirringby stirring at room temperature for one day
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. additiona saturated aqueous sodium hydrogen carbonate solution was added
  12. extractionfollowed by extraction with CHCl3
  13. dry with materialThe organic layer was dried over Na2SO4
  14. concentrationconcentrated under reduced pressure
  15. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)
  16. dissolutionThe product was dissolved in EtOH (3 ml)
  17. additionL-tartaric acid (126 mg) was added
  18. stirringby stirring at room temperature for 2 hours
  19. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-e5a84090f5984028b9960d40708846ad
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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