Diethylene Glycol Monomethyl Ether → N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid 2-(2-methoxy-ethoxy)ethyl ester

HRID 1797316

Reaktionsgleichung

Reaktionsgleichung von HRID 1797316
CCOC(/N=N/C(OCC)=O)=O.[Cl:13][C:14]1[CH:15]=[C:16]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][C:37](=[O:43])[CH2:38][CH2:39][C:40]([OH:42])=[O:41])[CH:17]=[CH:18][C:19]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:63][O:64][CH2:65][CH2:66][O:67][CH2:68][CH2:69]O>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH3:63][O:64][CH2:65][CH2:66][O:67][CH2:68][CH2:69][O:41][C:40](=[O:42])[CH2:39][CH2:38][C:37]([NH:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:29][C:16]1[CH:17]=[CH:18][C:19]([C:20](=[O:28])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])=[C:14]([Cl:13])[CH:15]=1)=[O:43]

Komponenten

8

Edukt 4

HCID 8134Diethylene Glycol Monomethyl EtherHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 9845903N-[2-[3-Chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]-succinamic Acid

Produkt 1

HCID 69663252N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid 2-(2-methoxy-ethoxy)ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of diethylazodicarboxylate (40% in toluene, 229 μL, 0.5 mmol) was slowly added to a mixture of N-(2-{[3-chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid (200 mg, 0.46 mmol) (disclosed in WO 01/05746), triphenylphosphine (132 mg, 0.50 mmol), and 2-(2-methoxyethoxy)ethanol (55 mg, 0.46 mmol) in dry toluene (2.5 ml). The reaction mixture was stirred for 48 h and then poured into a mixture of water and EtOAc. The aqueous phase was extracted with more EtOAc (×2). The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc as the eluent to afford the title compound as a yellow oil.

Aufarbeitung

  1. extractionThe aqueous phase was extracted with more EtOAc (×2)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3b3b7a0bd78c440686b1c6c5346051a3
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034015B2

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