9(S)-benzoylamino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1(S)-carboxylic acid → HCID 53667796, compound

HRID 2230452Notes

Reaction equation

HRID 2230452 reaction equation
[C:1]([NH:9][C@@H:10]1[C:16](=[O:17])[N:15]2[C@H:18](C(O)=O)[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:25])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[C:30]([NH:32][CH:33]([C:42](=[O:53])[CH2:43][O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[Cl:52])[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:31])C=C.C(NC1C(=O)N2C(C(NC(C(=O)CSCC3C=CC=CC=3Cl)CC(OC(C)(C)C)=O)=O)CCCN2C(=O)CC1)(=O)C1C=CC=CC=1>>[C:1]([NH:9][CH:10]1[C:16](=[O:17])[N:15]2[CH:18]([C:30]([NH:32][CH:33]([C:42](=[O:53])[CH2:43][O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[Cl:52])[CH2:34][C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])=[O:31])[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:25])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 183965489(S)-benzoylamino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1(S)-carboxylic acidHCID 18465693HCID 18465693, compoundHCID 18465758HCID 18465758, compound

Product 1

HCID 53667796HCID 53667796, compoundYield 23%

Procedure

was prepared from acid 212e and (3S) t-butyl N-(allyloxycarbonyl)-3-amino-5-(2-chorophenylmethyloxy)-4-oxopentanoate (201) using a method similar to that used for compound 224e, to afford 40 mg (23%) of a glassy solid: 1H NMR (CDCl3) δ7.83-7.73 (2H, m), 7.67-7.10 (9H, m), 5.23-5.09 (2H, m), 4.59 (1H, m), 4.45-4.22 (2H, m), 3.7-3.19, 3.08-2.72, 2.71-2.47, 2.05-1.85, 1.72-1.61, 1.45-1.26 (20H, 6 m).

Sources & evidence

ORD record
ord-0564e9b381a84d3495f48f11cfafb5b5
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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