Acetic Acid → 5-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 54746

Reaktionsgleichung

Reaktionsgleichung von HRID 54746
[OH:1][CH:2]1[C:8]2[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=2[N:6]([C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][C:16]=2[O:31][CH3:32])[CH2:5][CH2:4][CH2:3]1.CN([C:37]1[CH:42]=[CH:41]C=CN=1)C.Cl.CN(C1C=CC=CN=1)C.C(O[NH:58][C@H:59]([C:66]([OH:68])=O)[C:60](=C=O)[CH2:61][S:62][CH3:63])(C)(C)C.[CH:69]1(N=C=NC2CCCCC2)CCCCC1.[C:84]([OH:87])(=[O:86])C>C(Cl)(Cl)Cl.CO>[C:42]([O:87][C:84]([NH:58][C@H:59]([C:66]([O:1][CH:2]1[C:8]2[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=2[N:6]([C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][C:16]=2[O:31][CH3:32])[CH2:5][CH2:4][CH2:3]1)=[O:68])[CH2:60][CH2:61][S:62][CH3:63])=[O:86])([CH3:41])([CH3:37])[CH3:69]

Komponenten

9

Edukt 6

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 189174175-Hydroxy-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepineHCID 22461520Dimethylaminopyridine hydrochlorideHCID 86750746N-tert-butoxy-carbonyl-L-methionine

Produkt 1

HCID 228720795-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In 15 ml of chloroform were dissolved 0.7 g of 5-hydroxy-7-chloro-1-[2-methoxy-4-(2methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine, 0.83 g of dimethylaminopyridine and 0.72 g of dimethylaminopyridine hydrochloride. Thereto were added 0.56 g of N-tert-butoxy-carbonyl-L-methionine and 0.93 g of dicyclohexylcarbodi-imide. The mixture was stirred at room temperature for 3 hours. 3 ml of methanol and 0.7 ml of acetic acid were added, and the mixture was stirred at room temperature for 30 minutes. The resulting insolubles were removed by filtration. The filtrate was mixed with a 5% aqueous sodium hydrogensulfate solution, followed by extraction with dichloromethane. The dichloromethane layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution in this order and dried over magnesium sulfate. The resulting dichloromethane solution was concentrated for solvent removal. The residue was purified by silica gel column chromatography [elutant: dichloromethane/methanol=150/1] to obtain 1.27 g of 5-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzo-azepine.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. customThe resulting insolubles were removed by filtration
  3. additionThe filtrate was mixed with a 5% aqueous sodium hydrogensulfate solution
  4. extractionfollowed by extraction with dichloromethane
  5. washThe dichloromethane layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  6. dry with materiala saturated aqueous sodium chloride solution in this order and dried over magnesium sulfate
  7. concentrationThe resulting dichloromethane solution was concentrated for solvent removal
  8. customThe residue was purified by silica gel column chromatography [elutant: dichloromethane/methanol=150/1]

Quellen und Nachweise

ORD-Eintrag
ord-6540c8ed439b4d91a3b40376c4ba882f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622947

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