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Hydrochloric Acid → (R)-tert-Butyl 1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropylcarbamate

HRID 1373372
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1373372
[C:1]([O:5][C:6](=[O:31])[NH:7][C@@H:8]([CH:12]=[N:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[C:21](=[O:30])[NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>O1CCOCC1.C(O)CO>[C:1]([O:5][C:6](=[O:31])[NH:7][C@@H:8]([C:12]1[N:22]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:21](=[O:30])[C:15]2[C:14](=[CH:19][C:18]([Cl:20])=[CH:17][CH:16]=2)[N:13]=1)[CH:9]([CH3:11])[CH3:10])([CH3:3])([CH3:4])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69519159(R)-{1-[(2-benzylcarbamoyl-5-chloro-phenylimino)-methyl]-2-methyl-propyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 57351218(R)-tert-Butyl 1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22419261
Ethylene glycol dioxane
Lösungsmittel

Versuchsvorschrift

A dry 3-necked, round bottomed flask, equipped with a magnetic stirrer, nitrogen inlet, heating mantle and a water condenser, is charged with 60 mL of 1,4-dioxane/ethylene glycol (2:1), 4.60 g (10 mmol) of (R)-{1-[(2-benzylcarbamoyl-5-chloro-phenylimino)-methyl]-2-methyl-propyl}-carbamic acid tert-butyl ester (a compound of Formula 106, obtained as described in Example 5.3), and 0.46 g (11 mmol) of lithium hydroxide monohydrate. The mixture is heated to reflux and the reaction is monitored by TLC (hexanes/ethyl acetate 7:3). After 4 h of refluxing the reaction appears to be complete. The mixture is allowed to cool to room temperature and is slowly acidified to pH=5 by adding 1N hydrochloric acid. The mixture is stirred for 1 h and the white suspension is separated by filtration and dried in high vacuum to afford the title compound of Formula 107, (R)-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methylpropyl]-carbamic acid tert-butyl ester.

Aufarbeitung

  1. customA dry 3-necked, round bottomed flask, equipped with a magnetic stirrer, nitrogen inlet
  2. temperatureheating mantle and a water condenser
  3. customobtained
  4. temperatureThe mixture is heated
  5. temperatureto reflux
  6. temperatureAfter 4 h of refluxing the reaction
  7. customthe white suspension is separated by filtration
  8. customdried in high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-86139b0cab6f4759bb2f2aa653c07daa
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07161002B2

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