9(S)-benzoylamino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1(S)-carboxylic acid → HCID 18465736, compound

HRID 2230451Notes

Reaction equation

HRID 2230451 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][C@H:33]([CH:42]([OH:54])[C:43]1[O:44][C:45]2[C:51]([Cl:52])=[CH:50][C:49]([Cl:53])=[CH:48][C:46]=2[N:47]=1)[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)COCC3C(Cl)=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]([CH:42]([C:43]3[O:44][C:48]4[C:49]([Cl:53])=[CH:50][C:51]([Cl:52])=[CH:45][C:46]=4[N:47]=3)[OH:54])[CH2:34][C:35]([O:37][C:38]([CH3:40])([CH3:39])[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 18396559HCID 18396559, compoundHCID 54324685HCID 54324685, compound

Product 1

HCID 18465736HCID 18465736, compound

Procedure

was prepared from the acid (212e) and (3S,4RS) t-butyl N-(allyloxycarbonyl)-3-amino-4-hydroxy-4-(5,7-dichlorobenzoxazol-2-yl)butanoate (204) by an analogous method as that used for compound 215e to afford a mixture of diastereomers (613 mg, 87%) as a glass: IR film) 3328, 1229, 1660, 1534, 1454, 1422, 1399, 1276, 1254, 1155; 1H NMR (CDCl3) δ7.80 (2H, d), 7.60-7.35 (5H, m), 1155; 1H NMR (CDCl3) δ7.80 (2H, d), 7.60-7.35 (5H, m), 7.05 (2H, m), 5.13 (3H, m), 4.74 (1H, m), 4.51 (1H, m), 3.25 (1H, m), 3.1-2.6 (5H, m), 2.33 (1H, m), 2.1-1.5 (5H, m), 1.43 and 1.41 (9H combined, 2×s). MS ES+ Da/e 688 (M+1)+ Cl35 55%, 690 (M+1)+ Cl37 35%, 328 100%.

Workup

  1. customto afford
  2. additiona mixture of diastereomers (613 mg, 87%) as a glass

Sources & evidence

ORD record
ord-d3d344340c3d444ab8758990aa2ac980
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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