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1,1'-Carbonyldiimidazole → ethyl 2-amino-2-(((2-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoyl)oxy)imino)acetate

HRID 1477896
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1477896
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)([CH2:22][CH3:23])[C:19]([OH:21])=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:43][CH2:44][O:45][C:46](/[C:48](/[NH2:51])=[N:49]/O)=[O:47]>C(Cl)Cl.CCOC(C)=O>[NH2:51][C:48](=[N:49][O:20][C:19](=[O:21])[C:18]([N:13]1[C:14]2[C:10](=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:17]=[CH:16][CH:15]=2)[CH:11]=[N:12]1)([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH2:22][CH3:23])[C:46]([O:45][CH2:44][CH3:43])=[O:47]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 9614369Ethyl 2-oximinooxamateHCID 705627322-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoic acid

Produkt 1

HCID 86705053ethyl 2-amino-2-(((2-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoyl)oxy)imino)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 2-(4-((tert-butoxycarbonyl)amino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoic acid from Step A above (0.16 g, 0.37 mmol) in DCM (1.5 mL) was added 1,1′-carbonyldiimdazole (0.13 g, 0.78 mmol) to give a clear solution. The mixture was stirred for 7.5 hours at RT followed by addition of ethyl 2-oximinooxamate (0.13 g, 0.93 mmol). After stirring at RT overnight, the resulting mixture was diluted with EtOAc, washed with saturated NaHCO3 solution, water and brine. The organic layer was separated, and concentrated. The resulting crude product was re-dissolved in a mixture of acetonitrile and water and dried in a lyophilized to give the title compound as light yellow solid. LC/MS m/z=544.1 [M+H]+.

Aufarbeitung

  1. customto give a clear solution
  2. stirringAfter stirring at RT overnight
  3. washwashed with saturated NaHCO3 solution, water and brine
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. dissolutionThe resulting crude product was re-dissolved in a mixture of acetonitrile and water
  7. customdried in

Quellen und Nachweise

ORD-Eintrag
ord-d93b49d228e14e92ae8fb2593e744e86
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09403807B2

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