StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1,3-Cyclopentanedione → 3-({[(1R,2R,3S,6S)-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)-6-(hydroxymethyl)cyclohexyl]methyl}amino)cyclopent-2-en-1-one

HRID 2245244
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2245244
C([O:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C@@H:13]([C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[CH3:14])[C@@H:8]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C@@H:7]1[CH2:36][NH2:37])(=O)C.[C:38]1(=O)[CH2:42][CH2:41][C:40](=[O:43])[CH2:39]1>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[F:23][C:21]([F:24])([F:22])[C:19]1[CH:20]=[C:15]([C@H:13]([O:12][C@H:9]2[CH2:10][CH2:11][C@H:6]([CH2:5][OH:4])[C@@H:7]([CH2:36][NH:37][C:38]3[CH2:42][CH2:41][C:40](=[O:43])[CH:39]=3)[C@@H:8]2[C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[CH3:14])[CH:16]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 774661,3-CyclopentanedioneHCID 86628109HCID 86628109, Verbindung

Produkt 1

HCID 866281103-({[(1R,2R,3S,6S)-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)-6-(hydroxymethyl)cyclohexyl]methyl}amino)cyclopent-2-en-1-oneAusbeute 32,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysator
HCID 1140
Toluene
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 0.35 g (0.65 mmol) of [(1S,2R,3R,4S)-2-(aminomethyl)-4-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)cyclohexyl]methyl acetate (from Step N) in 30 mL dry toluene was added cyclopentane-1,3-dione (0.064 g, 0.65 mmol) and a catalytic amount (˜0.5 mg) of PTSA. The resulting mixture was heated at reflux for 1 hr. The solvent was removed under vacuum and the residue was dissolved in 30 mL methanol. Sodium hydroxide (15 mL, 5 N) was added and the resulting mixture was stirred at 50° C. for 2 hr. The methanol and some of water were removed under vacuum. Water (20 mL) was added and the aqueous layer was extracted with ethyl acetate (3×20 mL). The combined extracts were washed with brine, dried over Na2SO4 and the solvent was removed under vacuum. The residue was purified by prep. TLC (9:1 ethyl acetate:hexane) to give the title compound (0.12 g). 1H-NMR (CDCl3) δ: 7.70 (1H, s), 7.18 (2H, s), 6.98 (2H, m), 6.93 (2H, m), 5.18 (0.5H, bs), 4.67 (0.5H, bs), 4.22 (1H, m), 3.78 (1H, m), 3.47 (1H, m), 3.27 (1H, m), 3.07 (1H, m), 2.95 (1H, m), 2.30 (1H, t), 2.40-2.20 (5H, m), 1.90 (1H, m), 1.80 (1H, m), 1.70-1.20 (3H, m), 1.33 (3H, d, J=6.4 Hz). MS: (MH)+ 574.1.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1 hr
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in 30 mL methanol
  5. additionSodium hydroxide (15 mL, 5 N) was added
  6. customThe methanol and some of water were removed under vacuum
  7. additionWater (20 mL) was added
  8. extractionthe aqueous layer was extracted with ethyl acetate (3×20 mL)
  9. washThe combined extracts were washed with brine
  10. dry with materialdried over Na2SO4
  11. customthe solvent was removed under vacuum
  12. customThe residue was purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-d59ac65d0b0f41ad9c175bd606338b48
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07683068B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion