1,2-Dichloroethane → 3-[5-Oxo-pyrrolidine-2(S)-carbonylamino]-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine

HRID 609723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 609723
Br.[NH2:2][CH:3]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[NH:5][C:4]1=[O:20].[NH4+].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[Ce+4].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+].Br.C(O)(=O)C.[NH:65]1[C:69](=[O:70])[CH2:68][CH2:67][C@H:66]1[C:71](O)=[O:72].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(#N)C>[O:70]=[C:69]1[NH:65][C@H:66]([C:71]([NH:2][CH:3]2[N:9]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]3[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=3[NH:5][C:4]2=[O:20])=[O:72])[CH2:67][CH2:68]1

Komponenten

10

Edukt 7

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 180504Ceric ammonium nitrateHCID 6100505Dipotassium 2,3-dihydroxybutanedioateHCID 189176983-amino-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine hydrogen bromideHCID 86754905HBr acetic acid (L)-pyroglutamic acid

Produkt 1

HCID 229405853-[5-Oxo-pyrrolidine-2(S)-carbonylamino]-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 3-amino-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine hydrogen bromide (142 mg, 0.426 mmol), prepared by sequential treatment of an aqueous acetonitrile solution of the 4-methoxybenzyl derivative from example 5 with ammonium cerium IV nitrate, potassium tartrate solution and HBr/acetic acid-(L)-pyroglutamic acid (60.2 mg, 0.466 mmol), EDC (91 mg, 0.473 mmol), HOBT (63.5 mg, 0.473 mmol), and diisopropylethylamine (0.082 ml, 0.473 mmol) in DMF (5 ml) was stirred at room temperature for 18 hours. The resultant solution was concentrated in vacuo, and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic extract was washed with brine, dried, (MgSO4), filtered, and concentrated. The residue was purified by preparative HPLC (C18, eluted with a 5:95 to 40:60 water:acetonitrile). Lyophilization provided the titled compound as a 1:1 mixture of diastereomers.

Aufarbeitung

  1. concentrationThe resultant solution was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried, (MgSO4),
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative HPLC (C18
  9. washeluted with a 5:95 to 40:60 water

Quellen und Nachweise

ORD-Eintrag
ord-772ee2a01e944cc49e601f2e9601390d
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998407

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