Ethanol → N-formyl-3,4-dimethoxy-L-phenylalanine ethyl ester

HRID 275520Notes

Reaction equation

HRID 275520 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:19])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[NH2:7])[CH3:3].[CH:20]([O-])=[O:21].[Na+].C(OC(=O)C)(=O)C.C(O)C>C(O)=O>[CH2:2]([O:4][C:5](=[O:19])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[NH:7][CH:20]=[O:21])[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 2723810Sodium FormateHCID 186595423,4-dimethoxy-L-phenylalanine ethyl ester-hydrochloride

Product 1

HCID 10945877N-formyl-3,4-dimethoxy-L-phenylalanine ethyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a mixture of 3,4-dimethoxy-L-phenylalanine ethyl ester-hydrochloride 1 (Luxen, A., Perlmutter M., Bida, G. T., Van Moffaert, G., Cook, J. S., Satyamurthy, N., Phelps, M. E. and Barrio, J. R. (1990) Remote, semiautomated production of 6-[18F]fluoro-L-dopa for human studies with PET. Appl. Radiat. Isot. 41, 275) (5.3 g, 18.3 mmol) and sodium formate (1.44 g, 21.2 mmol) in formic acid (52 mL) cooled in an ice bath was added acetic anhydride (20 mL) and stirred at room temperature for 3 h. After addition of ethanol (40 mL) the mixture was stirred at room temperature for an additional 3 h and evaporated. The residue was dissolved in ethyl acetate, filtered and the insoluble material was washed with ethyl acetate. The combined filtrates were washed successively with aqueous 10% HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic extract was dried over anhydrous MgSO4 and concentrated under reduced pressure to a yellow syrup. Crystallization of the syrup from ethyl acetate-petroleum ether give a white solid 2 (3.1 g, 61%); m.p. 102°-103° C.

Workup

  1. stirringwas stirred at room temperature for an additional 3 h
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationfiltered
  5. washthe insoluble material was washed with ethyl acetate
  6. washThe combined filtrates were washed successively with aqueous 10% HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl
  7. extractionThe organic extract
  8. dry with materialwas dried over anhydrous MgSO4
  9. concentrationconcentrated under reduced pressure to a yellow syrup
  10. customCrystallization of the syrup from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-edf2186552da4aaea7656d80a16f77b4
Source dataset
uspto-grants-1995_02
Patent number
US05393908

Reaction notes

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