Chlorotrimethylsilane → N-(3,5dimethoxyphenyl)alanine iso-butyl ester

HRID 987771

Reaktionsgleichung

Reaktionsgleichung von HRID 987771
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C@H:12]([C:14]([OH:16])=[O:15])[CH3:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.COC1C=C([CH:23]=[C:24](OC)[CH:25]=1)N.Cl[CH:29](C)C(O)=O.Cl[Si](C)(C)C>C(O)C(C)C>[CH2:29]([O:15][C:14](=[O:16])[C@H:12]([CH3:13])[NH:11][C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH:24]([CH3:23])[CH3:25]

Komponenten

6

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 117342-Chloropropionic acidHCID 663013,5-DimethoxyanilineHCID 54357232N-(3,5-dimethoxyphenyl)alanine

Produkt 1

HCID 54083578N-(3,5dimethoxyphenyl)alanine iso-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6560IsobutanolLösungsmittel

Versuchsvorschrift

N-(3,5-dimethoxyphenyl)alanine (crude, 454 mg) (prepared according to the procedure described in U.S. Pat. No. 3,598,859 using 3,5-dimethoxyaniline (Aldrich) and 2-chloropropionic acid (Aldrich)) was treated in dry iso-butanol (10 mL) with 0.1 mL of chlorotrimethylsilane and the reaction mixture refluxed overnight. The excess alcohol was removed at reduced pressure and the residue dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated aqueous NaHCO3, dried with Na2SO4 and the solvent removed to provide the title compound. The reaction was monitored by silica gel tlc (Rf=0.3 in 20% EtOAc/hexanes). Purification was by preparative thin layer chromatography using 20% EtOAc/hexanes as the eluant.

Aufarbeitung

  1. temperaturethe reaction mixture refluxed overnight
  2. customThe excess alcohol was removed at reduced pressure
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed with saturated aqueous NaHCO3
  5. dry with materialdried with Na2SO4
  6. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-1b7d3551d7914846ba008cb13cdcd21c
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06632811B2

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