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1,1'-Carbonyldiimidazole → (2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-ethanoic acid

HRID 45617
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 45617
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N:20]1[C@H:25]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:24](=[O:30])[NH:23][C@H:22]([CH:31]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32]2)[C:21]1=[O:40])[C:10](NC1C=CC=CC=1O)=[O:11].C(N1C=CN=C1)(N1C=CN=C1)=[O:42]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N:20]1[C@H:25]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:24](=[O:30])[NH:23][C@H:22]([CH:31]2[CH2:32][C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:39]2)[C:21]1=[O:40])[C:10]([OH:42])=[O:11]
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Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 11649656(2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-hydroxyphenyl)ethanamide

Produkt 1

HCID 68844874(2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-ethanoic acidAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

(2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-N-(2-hydroxyphenyl)ethanamide (2.650 g) was stirred in dichloromethane (20 ml) and carbonyldiimidazole (1.178 g) was added. the mixture was left at room temperature for 16 hours then the solvent was removed under reduced pressure. The residue was then taken up in 1:1 acetone:water (v/v) (80 ml) and left at room temperature for 30 minutes. The bulk of the acetone was then removed under reduced pressure and the residue was partitioned between dichloromethane and 0.5M hydrochloric acid. The organic phase was separated (hydrophobic frit) and evaporated under reduced pressure. The crude product was purified (Biotage™ flash chromatography column, 90 g silica cartridge eluted with (i) 1:1 ethyl acetate:cyclohexane (ii) ethyl acetate (iii) ethyl acetate:methanol 9:1) to afford (2RS)-2-(2,4-difluorophenyl)-2-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-isobutyl-2,5-dioxopiperazin-1-yl]-ethanoic acid as a colourless solid 1.524 g as a mixture of epimers.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. waitwater (v/v) (80 ml) and left at room temperature for 30 minutes
  3. customThe bulk of the acetone was then removed under reduced pressure
  4. customthe residue was partitioned between dichloromethane and 0.5M hydrochloric acid
  5. customThe organic phase was separated (hydrophobic frit)
  6. customevaporated under reduced pressure
  7. customThe crude product was purified
  8. wash(Biotage™ flash chromatography column, 90 g silica cartridge eluted with (i) 1:1 ethyl acetate:cyclohexane (ii) ethyl acetate (iii) ethyl acetate:methanol 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-6e083c1a5e6148538aabf28d53f75cd1
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08541579B2

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