Trifluoroacetic acid water → 3-[4-Hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid methyl ester

HRID 1181042ノート

反応式

HRID 1181042 の反応式
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])(C)(C)C.C(C(O)=O)(F)(F)F.O>C(Cl)Cl>[CH3:1][O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19]

参加物

4

反応物 2

HCID 22392675Trifluoroacetic acid waterHCID 589794703-[4-Hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester

生成物 1

HCID 589789623-[4-Hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid methyl ester収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 3-[4-hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester (3.0 mmol, 1.0 g) in CH2Cl2 (10 mL) was treated with 90% CF3CO2H/H2O (20 mL) at ambient temperature. The mixture was stirred for 3 h and concentrated. The residue was dissolved in MeOH (20 mL), treated with conc. H2SO4 (1 mL), and heated at reflux for 14 h. The mixture was cooled and concentrated. The residue was dissolved in water/ethyl acetate and neutralized with K2CO3. The organic layer was dried (Na2SO4), and concentrated to give the title compound (0.76 g, 86%). HRMS Calculated for C15H22NO5: m/z 296.1498. Found: 296.1504.

後処理

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in MeOH (20 mL)
  3. additiontreated with conc. H2SO4 (1 mL)
  4. temperatureheated
  5. temperatureat reflux for 14 h
  6. temperatureThe mixture was cooled
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in water/ethyl acetate and neutralized with K2CO3
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-8386ebfd23a44964a787484a7afc6a20
出典データセット
uspto-grants-2007_10
特許番号
US07282501B2

反応ノート

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