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

Cesium carbonate → (3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide

HRID 736787
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 736787
[C:1]([O:5][NH:6][C:7]([C@:9]1([CH3:26])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:34][C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38]=[C:37]([CH3:45])[CH:36]=1>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][NH:6][C:7]([C@:9]1([CH3:26])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:34][C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:38]=[C:37]([CH3:45])[CH:36]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:8])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 115357194-(Chloromethyl)-2-methylquinolineHCID 86607887(3R,4R)-N-tert-butoxy-4-(4-hydroxyphenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxamide

Produkt 1

HCID 86607888(3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamideAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The crude (3R,4R)-N-tert-butoxy-4-(4-hydroxyphenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxamide (1.76 mmol) from Step 9 was dissolved in DMF (20 mL) and cesium carbonate (2.9 g, 8.80 mmol, 5.0 eq) and 4-chloromethyl-2-methylquinoline (602 mg, 2.64 mmol, 1.5 eq) were added. The mixture was stirred at room temperature overnight and then diluted with ethyl acetate (200 mL) and washed with water (100 mL×3). The aqueous layer was re-extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica eluting with 75% ethyl acetate/hexane to yield 0.53 g (56% for three steps) of (3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide as white solid. MS: (M+H)+=542.0

Aufarbeitung

  1. washwashed with water (100 mL×3)
  2. extractionThe aqueous layer was re-extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica eluting with 75% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-ebdfb3fa18d0467eab5eca3c7e828e05
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07595327B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion