Hydrochloric Acid → HCID 70039385, compound

HRID 369786Notes

Reaction equation

HRID 369786 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[O:4].Cl.OS(O)(=O)=O.[CH3:23][C:24](=[CH2:26])[CH3:25].C([O-])(O)=O.[Na+]>O1CCOCC1.CCOCC>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[CH2:8][C@@H:9]([C:11]([O:13][C:24]([CH3:26])([CH3:25])[CH3:23])=[O:12])[NH2:10])=[O:4]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 1118Sulfuric AcidHCID 8255Isobutylene2×HCID 516892Sodium BicarbonateHCID 18656092HCID 18656092, compound

Product 1

HCID 70039385HCID 70039385, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.88 g of 3-methoxycarbonyl-L-phenylalanine.HCl, and 1.5 mL of conc. H2SO4 in 20 mL of 1,4-dioxane was added to 25 mL of liquid isobutylene (condensed at -78° C. ) in a 300 mL pressure bottle equipped with a magnetic stirrer. The bottle was sealed and the mixture allowed to warm to RT with stirring. The initially heterogeneous mixture afforded a slightly cloudy solution after stirring for 18 h at RT. After 48 h the vessel was chilled in an ice water bath, opened, and the contents treated with 13 g of said NaHCO3. The isobutylene was allowed to evaporate and the remaining mixture was concentrated in vacuo to dryness. The residue was suspended in 100 mL of water and extracted with EtOAc (4×40 mL). The combined EtOAc extracts were washed with 5% aqueous NaHCO3 (3×50 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give an oil. This material was dissolved in 30 mL of ether and the solution was treated with 3.4 mL of 1 M ethereal HCl. A white solid precipitated which was collected by filtration and dried in vacuo to afford 0.79 g (74%) of tert-butyl 3-methoxycarbonyl-L-phenylalaninate.HCl, m.p. 165° C. (dec).

Workup

  1. customequipped with a magnetic stirrer
  2. customThe bottle was sealed
  3. customThe initially heterogeneous mixture afforded a slightly cloudy solution
  4. stirringafter stirring for 18 h at RT
  5. temperatureAfter 48 h the vessel was chilled in an ice water bath
  6. customto evaporate
  7. concentrationthe remaining mixture was concentrated in vacuo to dryness
  8. extractionextracted with EtOAc (4×40 mL)
  9. washThe combined EtOAc extracts were washed with 5% aqueous NaHCO3 (3×50 mL)
  10. dry with materialdried over anhydrous MgSO4
  11. concentrationconcentrated in vacuo
  12. customto give an oil
  13. customA white solid precipitated which
  14. filtrationwas collected by filtration
  15. customdried in vacuo

Sources & evidence

ORD record
ord-90d87f9a9fa646798cda370c35d652ea
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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