(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-(3,5-dimethyl-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

HRID 2230486Notes

Reaction equation

[O:1]=[C:2]1[N:8]([CH2:9]C(O)=O)[C:7]2[CH:13]=[CH:14][CH:15]=[CH:16][C:6]=2[N:5]([C:17](=[O:21])[CH2:18][O:19][CH3:20])[CH2:4][C@@H:3]1[NH:22][C:23](=[O:33])[C:24]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[C:26]([CH3:32])[CH:25]=1.O=C1N(C[C:43]([NH:45][C@H:46]2[CH2:50][C:49](=[O:51])[O:48][CH:47]2[O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[O:44])C2C=CC=CC=2N(C(=O)COC)C[C@@H]1NC(=O)C1C=C(Cl)C(O)=C(Cl)C=1.O=C1N(CC(O)=O)C2C=CC=CC=2N(C(=O)COC)C[C@@H]1NC(=O)C1C=C(Cl)C(O)=C(Cl)C=1>>[O:1]=[C:2]1[N:8]([CH2:9][C:43]([NH:45][C@H:46]2[CH2:50][C:49](=[O:51])[O:48][CH:47]2[O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[O:44])[C:7]2[CH:13]=[CH:14][CH:15]=[CH:16][C:6]=2[N:5]([C:17](=[O:21])[CH2:18][O:19][CH3:20])[CH2:4][C@@H:3]1[NH:22][C:23](=[O:33])[C:24]1[CH:25]=[C:26]([CH3:32])[C:27]([OH:31])=[C:28]([CH3:30])[CH:29]=1

Participants

Reactant 3

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-acetamide

HCID 66756266(3S)-2-Oxo-3-(3,5-dimethyl-4-hydroxybenzoyl)amino-5-methoxyacetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid

HCID 66756505(3S)-2-Oxo-3-(3,5-dichloro-4-hydroxybenzoyl)amino-5-methoxyacetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid

Product 1

HCID 22954566(3S)-2-Oxo-3-(3,5-dimethyl-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

Procedure

was synthesized from 687b by the method used to prepare 688a from 687a to afford 960 mg of 688b as an off-white solid, 1H NMR (CD3OD) δ2.6(dd, 1H), 2.7(dd, 1H), 3.0(dd, 1H), 3.2(s, 3H), 3.7(m, 3H), 3.9(m, 2H), 4.4-4.5(m, 2H), 4.6(m, 3H), 5.35(s, 1H), 5.55(d, 1H), 7.25(m, 2H), 7.4-7.5 (m, 4H).

Sources & evidence

ORD record: ord-3f07985ebebe47b184d0d6670b1a9c65
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06423840B1

Reaction notes

Loading…