HCID 53959266, compound → HCID 19783173, compound
Reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][CH:7]([C:17](=O)[CH2:18][CH2:19][CH2:20][CH3:21])[C:8](=NOC)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([F:25])[CH:3]=1.Cl.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:29]=1[NH:37][NH2:38]>>[Br:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[C:17]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:38][N:37]([C:29]3[CH:30]=[C:31]([N+:34]([O-:36])=[O:35])[CH:32]=[CH:33][C:28]=3[Cl:27])[C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([F:25])[CH:3]=1Participants
Procedure
By the procedure of Example 1, Step G, ethyl 3-(4-bromo-2-fluorobenzyl)-2-methoxyimino-4-oxooctanoate (from Step A) was reacted with 2-chloro-5-nitrophenylhydrazine hydrochloride. The crude product was flash chromatographed twice on silica gel (first column: gradient elution with 0.5-2% MeOH in CH2Cl2 ; second column: gradient elution with 5-20% EtOAc in hexane) to give a 54% yield of the title compound as an orange oil; homogeneous by TLC in 3:1 hexane-EtOAc; mass spectrum (FAB) m/e 538, 540 (M+1)+. 400 MHz 1H NMR (CDCl3) δ0.86 (t, J=7.3 Hz, 3H), 1.02 (t, J=7.1 Hz, 3H), 1.32 (m, 2H), 1.55 (m, 2H, partially obscured by H2O peak), 2.57 (t, J=7.8 Hz, 2H), 4.10 (s, 2H, superimposed on q, J=7.2 Hz, 2H), 6.82 (dd, J≈8, 8 Hz, 1H), 7.16 (d, J≈8 Hz, 1H), 7.23 (m, 1H, partially obscured by CHCl3 peak), 7.65 (d, J=8.8 Hz, 1H), 8.25 (dd, J=8.8, 2.6 Hz, 1H), 8.33 (d, J=2.6 Hz, 1H).
Workup
- customchromatographed twice on silica gel (first column: gradient elution with 0.5-2% MeOH in CH2Cl2 ; second column: gradient elution with 5-20% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-2b6874d7a15c440781a91a6f7122b3d3
- Source dataset
- uspto-grants-1993_11
- Patent number
- US05262412
Reaction notes
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