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 2230487Notes

Reaction equation

HRID 2230487 reaction equation
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

Participants

4

Reactant 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, compound2×

Product 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

Procedure

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).

Sources & evidence

ORD record
ord-a9bcb6c6e03542a0b6f3147e64202e7b
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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