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Water → ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate

HRID 1354547
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1354547
[CH2:1]([C@H:3]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[C:5](=[O:17])[CH2:4]1)[CH3:2].Cl.[CH2:19](O)[CH3:20].[OH2:22]>C(OCC)(=O)C>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([NH:6][C@H:3]([CH2:1][CH3:2])[CH2:4][C:5]([O:17][CH2:19][CH3:20])=[O:22])=[CH:8][CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinoneHCID 21887872Ethanol hydrochloride

Produkt 1

HCID 57888577ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To 200 mg (0.822 mmol) of (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone produced in Example 6, 2.0 g (16.45 mmol) of 30 wt % hydrogen chloride/ethanol solution was added dropwise for 5 minutes. On completion of the addition, the resulting solution was heated to 40° C. and stirred for 14 hours. Water (5 mL) was added to the solution and extraction with ethyl acetate was carried out. The extracted organic layer was washed with saturated brine and the product was dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate as a yellow oil (193.8 mg, crude yield: 82%). 1H-NMR (CDCl3, 400 MHz/ppm): 6 0.98 (3H, t), 1.23 (3H, t), 1.55-1.71 (2H, m), 2.53 (2H, m), 3.75-3.82 (1H, m), 4.11 (2H, q), 6.61 (2H, d), 7.38 (2H, d)

Aufarbeitung

  1. additionOn completion of the addition
  2. washThe extracted organic layer was washed with saturated brine
  3. dry with materialthe product was dried with anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-73fe19ce2e774848ad86095eb599e904
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07223859B2

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