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

HRID 2230488Notes

Reaction equation

HRID 2230488 reaction equation
C(OC(=O)CN1C2C=CC=CC=2NC[C@H](NC(OC(C)(C)C)=O)C1=O)C1C=CC=CC=1.[O:32]=[C:33]1[N:39]([CH2:40][C:41]([NH:43][C@H:44]2[CH2:48][C:47](=[O:49])[O:46][CH:45]2[O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[O:42])[C:38]2[CH:58]=[CH:59][CH:60]=[CH:61][C:37]=2[N:36]([C:62](=[O:66])[CH2:63]OC)[CH2:35][C@@H:34]1[NH:67][C:68](=[O:78])[C:69]1[CH:74]=[C:73](Cl)[C:72](O)=[C:71](Cl)[CH:70]=1>>[O:32]=[C:33]1[N:39]([CH2:40][C:41]([NH:43][C@H:44]2[CH2:48][C:47](=[O:49])[O:46][CH:45]2[O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[O:42])[C:38]2[CH:58]=[CH:59][CH:60]=[CH:61][C:37]=2[N:36]([C:62](=[O:66])[CH3:63])[CH2:35][C@@H:34]1[NH:67][C:68](=[O:78])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1

Participants

3

Reactant 2

HCID 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 22954569(3S)-2-Oxo-3-benzoylamino-5-acetyl-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 688a from 600b afford 30 mg of 693, 1H NMR (CD3OD) δ1.7(s, 3H), 1.8(s, 3H), 2.51(d, 1H, 2.6(m, 1H), 2.8(m, 1H), 3.0(m, 1H), 3.75(br. d, 2H), 4.0-4.1(dd, 2H), 4.5-5.0(m, 6H), 5.45(s, 1H), 5.55(s, 1H), 7.15-7.85(m, 14H).

Sources & evidence

ORD record
ord-22882444bf6f4ece8156e41a80e04ac9
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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