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

Dimethylformamide → (S)-2'-(cyclopropylethynyl)-7'-(2-methoxy-2-methylpropoxy)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 335769
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 335769
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:25]=1)[C:18]1[CH:17]=[C:16]([C:19]#[C:20][CH:21]3[CH2:23][CH2:22]3)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([OH:24])=[CH:9][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.I[CH2:38][C:39]([O:42][CH3:43])([CH3:41])[CH3:40]>O.CCOC(C)=O>[CH:21]1([C:20]#[C:19][C:16]2[CH:15]=[CH:14][C:13]3[O:12][C:11]4[C:6](=[CH:7][C:8]([O:24][CH2:38][C:39]([O:42][CH3:43])([CH3:41])[CH3:40])=[CH:9][CH:10]=4)[C@:5]4([CH2:4][O:3][C:2]([NH2:1])=[N:25]4)[C:18]=3[CH:17]=2)[CH2:23][CH2:22]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 189668321-Iodo-2-methoxy-2-methylpropaneHCID 67240959(S)-2-amino-2'-(cyclopropylethynyl)-5H-spiro[oxazole-4,9'-xanthen]-7'-ol

Produkt 1

HCID 58466161(S)-2'-(cyclopropylethynyl)-7'-(2-methoxy-2-methylpropoxy)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 2-5 mL microwave vial was charged with (S)-2-amino-2′-(cyclopropylethynyl)-5H-spiro[oxazole-4,9′-xanthen]-7′-ol (0.250 g, 0.752 mmol), cesium carbonate (0.980 g, 3.01 mmol), and DMF (3.01 mL). The mixture was stirred vigorously for 5 min, then 1-iodo-2-methoxy-2-methylpropane (0.303 mL, 2.257 mmol) was added via syringe. The vial was sealed and the reaction was microwaved at 110° C. for two hours. The mixture was diluted with water and EtOAc and the layers were separated, and the aqueous layer was extracted twice with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was purified by chromatography on a 12-g Redi-Sep column, eluting with 0-10% MeOH/DCM to provide (S)-2′-(cyclopropylethynyl)-7′-(2-methoxy-2-methylpropoxy)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as an off-white solid.

Aufarbeitung

  1. customThe vial was sealed
  2. customthe reaction was microwaved at 110° C. for two hours
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted twice with EtOAc
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on a 12-g Redi-Sep column
  9. washeluting with 0-10% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-829e75c3867b4877988f7abf68a58a28
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883782B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion