2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 14856087, compound
Reaction equation
[Cl:1][CH2:2][C:3](=[O:11])/[C:4](=[N:8]/[O:9][CH3:10])/[C:5]([OH:7])=O.[NH2:12][CH:13]1[C:38](=[O:39])[N:15]2[C:16]([C:27]([O:29][CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])=[O:28])=[C:17]([CH2:20][S:21][C:22]3[S:26][N:25]=[N:24][CH:23]=3)[CH2:18][S:19][C@H:14]12.C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C>C(Cl)Cl>[Cl:1][CH2:2][C:3](=[O:11])/[C:4](=[N:8]/[O:9][CH3:10])/[C:5]([NH:12][C@@H:13]1[C:38](=[O:39])[N:15]2[C:16]([C:27]([O:29][CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:37])[CH3:36])=[O:28])=[C:17]([CH2:20][S:21][C:22]3[S:26][N:25]=[N:24][CH:23]=3)[CH2:18][S:19][C@H:14]12)=[O:7]Participants
Procedure
A solution of 4-chloro-2-(Z)-methoxyimino-3-oxo-butanoic acid (2.17 g, 4.77 mmol.), 2-(trimethylsilyl)ethoxymethyl 7-amino-3-[(1,2,3-thiadiazol-5-yl)thiomethyl]ceph-3-em-4-carboxylate (0.85 g, 4.77 mmol.), and 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (1.18 g, 4.77 mmol.) in 40 ml of methylene chloride was stirred at room temperature for 3 hours then worked up as described in Example 6 to afford 0.615 g of the ester. NMR (CDCl3) δ0.03 [S, 9H, --Si(CH3)3 ], 0.97 (t, 2H, J=7.5 Hz, --CH2Si--), 3.62 (pair of d, 2H, J=18 Hz, endocyclic --CH2S--), 3.75 (m, 2H, --OCH2 --), 4.17 (pair of d, 2H, J=3 Hz, exocyclic --CH2S), 4.18 (S, 3H, --OCH3), 4.63 (S, 2H, --ClCH2 --), 5.07 (d, 1H, J=4.9, 6H of 7ACA), 5.38 (pair of d, 2H, J=6.0 Hz, --OCH2O), 5.87 (dd, 1H, J=4.9 and 8.5 Hz, 7H of 7ACA), 7.22 (d, 1H, J=8.5 Hz, --NH--), 8.52 (S, 1H, thiadiazole H).
Sources & evidence
- ORD record
- ord-be7ac28b793a4244b4431ebd0fd6c756
- Source dataset
- uspto-grants-1991_11
- Patent number
- US05066799
Reaction notes
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