9(S)-benzoylamino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1(S)-carboxylic acid → 9-Benzoylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-N-(2-(4-chlorobenzyl)oxy-5-oxotetrahydrofuran-3-yl)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide

HRID 2230477Notes

Reaction equation

HRID 2230477 reaction equation
C(N[C@@H]1C(=O)N2[C@H](C(O)=O)CCCN2C(=O)CC1)(=O)C1C=CC=CC=1.[C:26]([NH:34][CH:35]1[C:41](=[O:42])[N:40]2[CH:43]([C:47]([NH:49][CH:50]3[CH2:54][C:53](=[O:55])[O:52][CH:51]3[O:56][CH2:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[O:48])[CH2:44][CH2:45][CH2:46][N:39]2[C:38](=[O:64])[CH2:37][CH2:36]1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(OC(N[C@H]1CC(=O)OC1OCC1C=CC([Cl:86])=CC=1)=O)C=C>>[C:26]([NH:34][CH:35]1[C:41](=[O:42])[N:40]2[CH:43]([C:47]([NH:49][CH:50]3[CH2:54][C:53](=[O:55])[O:52][CH:51]3[O:56][CH2:57][C:58]3[CH:59]=[CH:60][C:61]([Cl:86])=[CH:62][CH:63]=3)=[O:48])[CH2:44][CH2:45][CH2:46][N:39]2[C:38](=[O:64])[CH2:37][CH2:36]1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 183965489(S)-benzoylamino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1(S)-carboxylic acid2×HCID 184657299-Benzoylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-N-(2-benzyloxy-5-oxotetrahydrofuran-3-yl)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamideHCID 59947520(3S,2RS) 3-Allyloxycarbonylamino-2-(4-chlorobenzyl)oxy-5-oxotetrahydrofuran

Product 1

HCID 184658349-Benzoylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-N-(2-(4-chlorobenzyl)oxy-5-oxotetrahydrofuran-3-yl)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide

Procedure

was synthesized from 212e by the methods used to prepare 213e from 212e using 2101a to afford 380 mg of 2100f, 1H NMR (CDCl3) δ1.8-2.0(m, 10H), 2.30(d, 1H), 2.31-2.5(m, 3H), 2.7-2.9(m, 3H), 3.05(m, 2H), 3.1-3.2(m, 4H), 4.45(q, 1H), 4.5-4.6(m, 3H), 4.7(d, 2H), 4.85(d, 1H), 4.9(t, 1H), 5.2(t, 1H), 5.15(m, 2H), 5.25(s, 1H), 5.55(d, 1H), 6.5(d, 1H), 6.9(d, 1H), 6.95(d, 1H), 7.25(m, 3H), 7.35(t, 2H), 7.45(m, 2H), 7.55(1H), 7.8(m, 3H).

Sources & evidence

ORD record
ord-f1c0fcda992045e6a3d93b49bfab918c
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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