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Trifluoroacetic acid → (S)-4-(biphenyl-4-yl)-3-[(dimethylphosphonomethyl)-amino]-butyric acid methyl ester

HRID 1655286
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1655286
[CH3:1][O:2][C:3](=[O:27])[C@@H:4](N)[CH:5](C(OC(C)(C)C)=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.FC(F)(F)C(O)=O.C([N:38]([CH:41](C)C)CC)(C)C.FC(S(OC[P:53]([O:57][CH3:58])([O:55][CH3:56])=[O:54])(=O)=O)(F)F>C(OCC)(=O)C.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C@@H:5]([NH:38][CH2:41][P:53]([O:57][CH3:58])([O:55][CH3:56])=[O:54])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][CH:12]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 22098913Dimethylphosphonomethyl trifluoromethylsulfonateHCID 70084322(S)-3-t-Butoxycarbonyl-amino-4-(biphenyl-4-yl)-butyric acid methyl ester

Produkt 1

HCID 54030507(S)-4-(biphenyl-4-yl)-3-[(dimethylphosphonomethyl)-amino]-butyric acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S)-3-t-Butoxycarbonyl-amino-4-(biphenyl-4-yl)-butyric acid methyl ester (716 mg, 2 mmol) is stirred for 1 hour in a 1/l mixture of trifluoroacetic acid and methylene chloride (5 mL). Ethyl acetate (20 mL) is added and the solution is washed with saturated sodium bicarbonate (20 mL). The organic layer is separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue is dissolved in methylene chloride (10 mL) and cooled to 0° under nitrogen. Diisopropyl ethylamine (0.42 mL, 2.4 mmol) is added, followed by a solution of dimethylphosphonomethyl trifluoromethylsulfonate (Tetrahedron Lett., 1986, 1477; 545 mg, 2.2 mmol). The mixture is stirred for 18 hours at room temperature. The solution is washed with saturated sodium bicarbonate, water and brine. The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash-chromatography to afford (S)-4-(biphenyl-4-yl)-3-[(dimethylphosphonomethyl)-amino]-butyric acid methyl ester as a white solid, m.p. 67°.

Aufarbeitung

  1. washthe solution is washed with saturated sodium bicarbonate (20 mL)
  2. customThe organic layer is separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in methylene chloride (10 mL)
  7. temperaturecooled to 0° under nitrogen
  8. washThe solution is washed with saturated sodium bicarbonate, water and brine
  9. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue is purified by flash-chromatography

Quellen und Nachweise

ORD-Eintrag
ord-04221892e8b8455bbada9953fc78b519
Quelldatensatz
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05250522

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