2-Oxo-3-benzoylamino-5-acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid → (3S)-2-Oxo-3-(3,5-dichloro4-hydroxybenzoyl)amino-5-hydroxyacetyl-N-[(2RS,3S)-benzyloxy-5-oxo-tetrahydrofuran-3-yl]-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetamide

HRID 2230487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2230487
C(OC(=O)CN1C2C=CC=CC=2NC[C@H](NC(OC(C)(C)C)=O)C1=O)C1C=CC=CC=1.O=C1N(CC(O)=O)C2C=CC=CC=2N(C(=O)C)CC1NC(=O)C1C=CC=CC=1.[O:60]=[C:61]1[N:67]([CH2:68][C:69]([NH:71][C@H:72]2[CH2:76][C:75](=[O:77])[O:74][CH:73]2[O:78][CH2:79][C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)=[O:70])[C:66]2[CH:86]=[CH:87][CH:88]=[CH:89][C:65]=2[N:64]([C:90](=[O:94])[CH2:91][O:92]C)[CH2:63][C@@H:62]1[NH:95][C:96](=[O:106])[C:97]1[CH:102]=[C:101]([Cl:103])[C:100]([OH:104])=[C:99]([Cl:105])[CH:98]=1>>[O:60]=[C:61]1[N:67]([CH2:68][C:69]([NH:71][C@H:72]2[CH2:76][C:75](=[O:77])[O:74][CH:73]2[O:78][CH2:79][C:80]2[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=2)=[O:70])[C:66]2[CH:86]=[CH:87][CH:88]=[CH:89][C:65]=2[N:64]([C:90](=[O:94])[CH2:91][OH:92])[CH2:63][C@@H:62]1[NH:95][C:96](=[O:106])[C:97]1[CH:98]=[C:99]([Cl:105])[C:100]([OH:104])=[C:101]([Cl:103])[CH:102]=1

Komponenten

4

Edukt 3

HCID 184657172-Oxo-3-benzoylamino-5-acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acidHCID 22954562(3S)-2-Oxo-3-(3,5-dichloro-4-hydroxybenzoyl)amino-5-methoxyacetyl-N-[(2RS,3S)-benzyloxy-5-oxo-tetrahydrofuran-3-yl]-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetamideHCID 57313411HCID 57313411, Verbindung2×

Produkt 1

HCID 22954561(3S)-2-Oxo-3-(3,5-dichloro4-hydroxybenzoyl)amino-5-hydroxyacetyl-N-[(2RS,3S)-benzyloxy-5-oxo-tetrahydrofuran-3-yl]-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetamide

Versuchsvorschrift

was synthesized from 600b via methods used to prepare 661 from 600b, excluding steps used to make 604d from 603d, using instead the method to prepare 688a from 678a to afford 854 mg of 692a, 1H NMR (CD3OD) δ2.45(d, 1H), 2.6(m, 1H), 2.7(m, 1H), 3.0(m, 1H), 3.5-3.7(m, 4H), 4.0(q, 2H), 4.45(m,3H), 4.55(m, 4H), 5.35(s, 1H), 5.6(d, 1H), 7.2-7.5(m, 9H), 7.85(s, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-a9bcb6c6e03542a0b6f3147e64202e7b
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423840B1

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