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Benzyl 4-Hydroxybenzoate → benzyl (S)-4-(2-amino-1-propoxy)benzoate

HRID 350567
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 350567
C(OC([NH:8][C@@H:9]([CH3:12])[CH2:10][OH:11])=O)(C)(C)C.O[C:14]1[CH:29]=[CH:28][C:17]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[CH:16][CH:15]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[NH2:8][C@@H:9]([CH3:12])[CH2:10][O:11][C:14]1[CH:29]=[CH:28][C:17]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[CH:16][CH:15]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7180Benzyl 4-HydroxybenzoateHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Produkt 1

HCID 86587801benzyl (S)-4-(2-amino-1-propoxy)benzoateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled (0° C.), stirred solution of (S)-2-(N-tert-butoxycarbonylamino)-1-propanol (6.74 g, 0.04 mol), benzyl 4-hydroxybenzoate (8.78 g, 0.04 mol), and Ph3P (15.13 g, 0.06 mol) in THF (100 ml) was added DIAD (11.4 ml, 0.06 mol), and the reaction mixture was heated under reflux overnight. The solution was evaporated and the residue was dissolved in CH2Cl2 (30 ml) and TFA (30 ml). The solution was stirred at room temperature for 30 min. and the solution was concentrated in vacuo. The residue was dissolved in CHCl3, washed with sat. NaHCO3, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica-gel with CHCl3 to CHCl3-MeOH (9:1, v/v) as eluent to give benzyl (S)-4-(2-amino-1-propoxy)benzoate (6.63 g, 2 steps, 60%) as a yellow oil. 1H-NMR (CDCl3) δ 1.18 (d, J=6.3 Hz, 3 H), 3.35–3.39 (m, 1 H), 3.71–3.75 (m, 1 H), 3.90–3.93 (m, 1 H), 5.34 (s, 2 H), 6.90–6.93 (m, 2H), 7.32–7.46 (m, 5H), 8.01–8.04 (m, 2H).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. customThe solution was evaporated
  4. dissolutionthe residue was dissolved in CH2Cl2 (30 ml)
  5. concentrationthe solution was concentrated in vacuo
  6. dissolutionThe residue was dissolved in CHCl3
  7. washwashed with sat. NaHCO3
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customThe residue was purified by column chromatography on silica-gel with CHCl3 to CHCl3-MeOH (9:1

Quellen und Nachweise

ORD-Eintrag
ord-4b663343c5814ec795fbabd49f7d85af
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07179819B2

Notizen zur Reaktion

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