Benzaldehyde → HCID 57014776, compound

HRID 342143Notes

Reaction equation

HRID 342143 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N([CH2:22][CH3:23])CC)C.S([O-])([O-])(=O)=O.[Mg+2].[CH3:30][C:31](C)([O-])C.[K+].S([O-])(=O)(=O)C>ClCCl.C1COCC1.CCOC(C)=O>[C:10]1([CH2:9][N:7]=[C:6]([CH2:30][C:31]#[C:22][CH3:23])[C:5]([O:4][CH2:2][CH3:3])=[O:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

10

Reactant 6

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 85257MethanesulfonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 57014776HCID 57014776, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of glycine ethyl ester hydrochloride (10.11 g, 72.4 mmol) in 200 mL of dichloromethane was added benzaldehyde (7.36 mL, 72.4 mmol), triethylamine (20.0 mL, 143 mmol), and magnesium sulfate (6 g). The solution was stirred at room temperature for 16 hours, filtered through a glass frit, and concentrated in vacuo. The residue was partitioned between ether and water, and the organic layer was washed with brine. The solution was dried over Na2SO4, filtered, and concentrated in vacuo to provide a pale yellow oil. A portion of this oil (9.90 g, 51.8 mmol) was dissolved in 200 mL of THF and cooled to -78° C. under nitrogen atmosphere. A solution of potassium tert-butoxide in THF (51.8 mL of 1M, 51.8 mmol) was added dropwise to produce a bright red solution. After 20 minutes, a solution of the mesylate from Step A (8.05 g, 54,4 mmol) in 20 mL of THF was added dropwise via cannula, and the solution was allowed to warm to room temperature. After 2 hours, the reaction was poured into EtOAc and washed with sat. NaHCO3 soln. and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled product.

Workup

  1. filtrationfiltered through a glass frit
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ether and water
  4. washthe organic layer was washed with brine
  5. dry with materialThe solution was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a pale yellow oil
  9. temperaturecooled to -78° C. under nitrogen atmosphere
  10. customto produce a bright red solution
  11. waitAfter 20 minutes
  12. temperatureto warm to room temperature
  13. waitAfter 2 hours
  14. washwashed with sat. NaHCO3 soln
  15. dry with materialand brine, dried (Na2SO4)
  16. filtrationfiltered
  17. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70052dd7c1a74158bbc61affe3f0d4d8
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

Loading…