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

HRID 1181042노트

반응식

HRID 1181042 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8386ebfd23a44964a787484a7afc6a20
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282501B2

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