Acetic Acid → Diethyl [2-(4-(4-chlorobenzoyl)-2-oxo-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-2,3,4,5-tetrahydro-1H-benzo-[e][1,4]-diazepin-8-yl)ethyl]phosphonate

HRID 2417490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2417490
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([N:8]([CH2:27][C:28](OCC)=[O:29])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][C:11]=2[NH2:26])=[O:7])=[CH:4][CH:3]=1.[N:35]1([C:40]([C:42]2[CH:49]=[CH:48][C:45]([CH:46]=O)=[CH:44][CH:43]=2)=[O:41])[CH2:39][CH:38]=[CH:37][CH2:36]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>ClCCl.[OH-].[Na+].C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][P:18](=[O:19])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:12][C:11]=3[N:26]([CH2:46][C:45]3[CH:44]=[CH:43][C:42]([C:40]([N:35]4[CH2:39][CH:38]=[CH:37][CH2:36]4)=[O:41])=[CH:49][CH:48]=3)[C:28](=[O:29])[CH2:27]2)=[O:7])=[CH:33][CH:34]=1

Komponenten

10

Edukt 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 86589876HCID 86589876, Verbindung

Produkt 1

HCID 60123508Diethyl [2-(4-(4-chlorobenzoyl)-2-oxo-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-2,3,4,5-tetrahydro-1H-benzo-[e][1,4]-diazepin-8-yl)ethyl]phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

180 mg (0.35 mmol) of ethyl ((4-chlorobenzoyl)-(4-(2-(diethoxyphosphoryl)ethyl)-2-aminobenzyl)amino)acetate and 92 mg (0.46 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde were dissolved in 10 ml of dichloromethane. 0.040 ml (0.7 mmol) of acetic acid was added to the obtained solution. They were stirred at room temperature for 30 minutes. 185 mg (0.88 mmol) of sodium triacetoxyborohydride was added to the obtained mixture and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in a mixture of 2 ml of 1 N sodium hydroxide and 4 ml of ethanol, and the obtained solution was stirred at room temperature for 5 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 10 ml of dichloromethane. 78 mg (0.46 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.15 ml (1.05 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. The solvent was evaporated and the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

Aufarbeitung

  1. stirringwere stirred at room temperature overnight
  2. stirringthe obtained solution was stirred at room temperature for 5 hours
  3. stirringwere stirred overnight
  4. customThe solvent was evaporated
  5. customthe obtained crude product
  6. additionwas treated in the same manner as in step 3 in Example 1

Quellen und Nachweise

ORD-Eintrag
ord-eab4cf856a944fe5a447eefc3e7f91ce
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825191B2

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