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

HRID 1721524ノート

反応式

HRID 1721524 の反応式
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].FN[C@@H](CC1C=C(O)C(O)=CC=1)[C:23](O)=[O:24].C([O-])=O.[Na+].C(OC(=O)C)(=O)C>C(O)=O.C(O)C>[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:23]=[O:24])[CH3:3]

参加物

7

反応物 4

HCID 7918Acetic AnhydrideHCID 2723810Sodium FormateHCID 186595423,4-dimethoxy-L-phenylalanine ethyl ester-hydrochlorideHCID 53962907fluoro-L-dopa

生成物 1

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

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-230b87c8ddbc4d1c8eb9addfb4309a32
出典データセット
uspto-grants-1996_04
特許番号
US05510522

反応ノート

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