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Diethyl Ether → 5-(4-fluorophenyl)-1-(2-((2S,4S)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide

HRID 5694
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 5694
[NH2:1][CH2:2][CH2:3][C@H:4]1OC(C)(C)[O:7][C@@H:6]([CH2:12][C:13]([OH:15])=[O:14])[CH2:5]1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[CH:24]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:25]([C:35](=O)[CH:36]([CH3:38])[CH3:37])[C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:27])=[CH:19][CH:18]=1.C(OCC)C.[Cl-].[NH4+]>CS(C)=O.O>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[N:1]([CH2:2][CH2:3][C@H:4]3[CH2:5][C@H:6]([OH:7])[CH2:12][C:13](=[O:14])[O:15]3)[C:35]([CH:36]([CH3:38])[CH3:37])=[C:25]([C:26]([NH:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:27])[C:24]=2[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:21][CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 99098724-(4-Fluorophenyl)-2-(2-methyl-1-oxopropyl)-4-oxo-3,N-diphenylbutanamideHCID 117906292-[(4R,6R)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic Acid

Produkt 1

HCID 139236655-(4-fluorophenyl)-1-(2-((2S,4S)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide
Ausbeute 24,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A solution of 0.26 g (1.21 mmol) of (±)-cis-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid and 0.504 g (1.20 mmol) of (±)4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)] and [S-(R*,S*)] isomers in 5 mL of dimethyl sulfoxide is heated at 105° C. for 15 hours. The solution is cooled and poured into 100 mL of diethyl ether and 50 mL of saturated ammonium chloride in water. The layers are separated and the organic layer washed with water (2×50 mL) and 5% sodium hydroxide solution (2×100 mL--to extract the intermediate from unreacted diketone). The aqueous layer is acidified with dilute hydrochloric acid solution and extracted with 30 mL of ethyl acetate. A drop of concentrated hydrochloric acid is added to the ethyl acetate solution and allowed to stand 18 hours. The solution is concentrated in vacuo and the concentrate is redissolved in 30 mL of ethyl acetate treated with one drop of concentrated hydrochloride acid. The solution is stirred two hours, concentrated in vacuo, and dissolved in 6 mL of toluene. Trans-(±)-5 -(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2 H-pyran-2-yl)ethyl]-1 H-pyrrole-3-carboxamide crystallizes and is isolated by filtration. A total of 0.16 g of trans-(±)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2 H-pyran-2-yl)ethyl]-1 H-pyrrole-3-carboxamide is isolated in two crops.

Aufarbeitung

  1. temperatureThe solution is cooled
  2. customThe layers are separated
  3. washthe organic layer washed with water (2×50 mL) and 5% sodium hydroxide solution (2×100 mL
  4. extractionto extract the intermediate from unreacted diketone)
  5. extractionextracted with 30 mL of ethyl acetate
  6. additionA drop of concentrated hydrochloric acid is added to the ethyl acetate solution
  7. concentrationThe solution is concentrated in vacuo
  8. dissolutionthe concentrate is redissolved in 30 mL of ethyl acetate
  9. additiontreated with one drop of concentrated hydrochloride acid
  10. concentrationconcentrated in vacuo
  11. dissolutiondissolved in 6 mL of toluene
  12. customTrans-(±)-5 -(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2 H-pyran-2-yl)ethyl]-1 H-pyrrole-3-carboxamide crystallizes
  13. customis isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e9af0c16de3b42cea332fbbddd9d1440
Quelldatensatz
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05245047

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