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

HRID 133344

反応式

HRID 133344 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6560Isobutanol溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-78978df8cf22445a86d6bae80f60f5e4
出典データセット
uspto-grants-2008_06
特許番号
US07390801B2

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