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

Acetonitrile → (R)-Methyl 3-(1-naphthamido)-2,3-dihydro-1H-indene-5-carboxylate

HRID 1193275
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1193275
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C([NH:15][CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=2)[CH2:18][CH2:17]1)(C)(C)C.CCN([CH:35]([CH3:37])[CH3:36])C(C)C.[C:38](#N)C>CN(C1C=CN=CC=1)C>[C:3]1([C:4]([NH:15][C@H:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=3)[CH2:18][CH2:17]2)=[O:5])[C:2]2[C:10](=[CH:38][CH:37]=[CH:35][CH:36]=2)[CH:9]=[CH:8][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 691102-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 66798482methyl 3-(tert-butylamino)-2,3-dihydro-1H-indene-5-carboxylate

Produkt 1

HCID 66799274(R)-Methyl 3-(1-naphthamido)-2,3-dihydro-1H-indene-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14284
4-(Dimethylamino)pyridine
Katalysator

Versuchsvorschrift

2-Chlorobenzoic acid chloride (7.0 g, 40.485 mmol, 10.0 eq.) was added at 0° C. to a solution of methyl 3-(tert-butylamino)-2,3-dihydro-1H-indene-5-carboxylate (A-16) (1.0 g, 4.0485 mmol, 1.0 eq.), DMAP (980 mg, 8.097 mmol, 2.0 eq.) and DIPEA (14 ml, 8.9716 mmol, 20.0 eq.) in acetonitrile (40 ml), and the mixture was then refluxed for 20 hours. After monitoring by TLC, the reaction solution was concentrated and the residue was taken up in ethyl acetate (300 ml), washed with sat. sodium hydrogen carbonate solution (100 ml), water (100 ml) and sat. NaCl solution (100 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 10% ethyl acetate in hexane). Yield: 2.0 g

Aufarbeitung

  1. temperaturethe mixture was then refluxed for 20 hours
  2. concentrationthe reaction solution was concentrated
  3. washwashed with sat. sodium hydrogen carbonate solution (100 ml), water (100 ml) and sat. NaCl solution (100 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography (silica gel, 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-952d70ecf6cb4d7e952dda0bddae3de1
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680159B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion