Dicyclohexylcarbodiimide → (S)-2-(1-(3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethyl)isoindoline-1,3-dione

HRID 57387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57387
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)/[C:5](=[N:7]/[OH:8])/[NH2:6].[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[C@@H:23]([CH3:27])[C:24](O)=O.C(=NC1CCCCC1)=NC1CCCCC1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:27]([C@@H:23]([N:14]3[C:15](=[O:22])[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:13]3=[O:12])[CH3:24])[O:8][N:7]=2)[CH:9]=[CH:10][CH:11]=1

Komponenten

4

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 720644Pht-Ala-OHHCID 95828343-chloro-N'-hydroxybenzenecarboximidamide

Produkt 1

HCID 90414565(S)-2-(1-(3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethyl)isoindoline-1,3-dione

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of (Z)-3-chloro-N′-hydroxybenzimidamide (500 mg, 2.93 mmol) and (S)-2-(1,3-dioxoisoindolin-2-yl)propanoic acid (642 mg, 2.93 mmol) was added N,N′-methanediylidenedicyclohexanamine (1.1 eq, 665 mg, 3.22 mmol) and allowed to reflux at 100° C. for 12 hours. Concentrate in vacuo, dilute w/EtOAc, filter washing w/EtOAc, wash w/water, brine, concentrate in vacuo. Flash column chromatography (silica, 40 g) eluting w/0-10% EtOAc/DCM afforded 300 mg. HRMS m/z 353.0567

Aufarbeitung

  1. concentrationConcentrate in vacuo
  2. additiondilute w/EtOAc
  3. filtrationfilter
  4. washwashing
  5. washwash w/water, brine
  6. concentrationconcentrate in vacuo
  7. washFlash column chromatography (silica, 40 g) eluting w/0-10% EtOAc/DCM
  8. customafforded 300 mg

Quellen und Nachweise

ORD-Eintrag
ord-7c8cb4017f714552a7782879abcbc5bb
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

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