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4-Methylmorpholine → HCID 86592732, Verbindung

HRID 2251909
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2251909
CN1CCOCC1.[CH3:8][N:9]([CH3:27])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([N:19]2[CH2:26][CH2:25][CH2:24][C@@H:20]2[C:21]([OH:23])=O)=[O:18])=[CH:12][CH:11]=1.ClC(OCC)=O.Cl.[Br:35][C:36]1[CH:50]=[C:49]([Cl:51])[CH:48]=[CH:47][C:37]=1[CH2:38][O:39][C:40]1[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=1[NH2:42]>O.C1(C)C=CC=CC=1>[Br:35][C:36]1[CH:50]=[C:49]([Cl:51])[CH:48]=[CH:47][C:37]=1[CH2:38][O:39][C:40]1[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=1[NH:42][C:21]([C@H:20]1[CH2:24][CH2:25][CH2:26][N:19]1[C:17](=[O:18])[CH2:16][C:13]1[CH:12]=[CH:11][C:10]([N:9]([CH3:8])[CH3:27])=[CH:15][CH:14]=1)=[O:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 79724-Methylmorpholine2×HCID 10928Ethyl chloroformateHCID 22934170Benzenamine, 2-[(2-bromo-4-chlorophenyl)methoxy]-, hydrochlorideHCID 57426175HCID 57426175, Verbindung

Produkt 1

HCID 86592732HCID 86592732, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Toluene (111 ml) and N-methylmorpholine (3.85 ml, 35.0 mmol) were added to N-[(4-dimethylaminophenyl)acetyl]-D-proline (8.56 g, 31.0 mmol). Ethyl chloroformate (3.26 ml, 34.1 mmol) was added to the obtained mixture, and they were stirred for 2 hours. 2-(2-Bromo-4-chlorobenzyloxy)aniline hydrochloride (10.8 g, 31.0 mmol) and N-methylmorpholine (4.09 ml, 37.2 mmol) were added thereto and they were stirred at room temperature overnight. Water (40 ml) was added to the reaction mixture. The organic layer was washed with water (40 ml) and then dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to the silica gel column chromatography. After the elution with methylene chloride and methanol (30:1), suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain the title compound in the form of a yellow solid (16.3 g, 92%).

Aufarbeitung

  1. stirringthey were stirred at room temperature overnight
  2. washThe organic layer was washed with water (40 ml)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washAfter the elution with methylene chloride and methanol (30:1), suitable fractions
  6. customwere collected
  7. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-20eeae9889964b38a20173f832a627fd
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07320973B2

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