Tert-butyl 3-cyanobenzyl(2-methoxyethyl)carbamate → tert-Butyl 3-[amino(hydroxyimino)methyl]benzyl(2-methoxyethyl)carbamate
Reaction equation
[NH2:1][C:2](=[N:15][OH:16])[C:3]1[CH:12]=[CH:11][C:6](C(OC)=O)=[CH:5][C:4]=1OC.C(C1C=C(C=CC=1)[CH2:22][N:23]([CH2:31][CH2:32][O:33][CH3:34])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])#N>>[NH2:1][C:2](=[N:15][OH:16])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:11][CH:12]=1)[CH2:22][N:23]([CH2:31][CH2:32][O:33][CH3:34])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]Participants
3
Procedure
Title compound was prepared following procedure and work up described for Intermediate 47 step 2 but starting from tert-Butyl 3-cyanobenzyl(2-methoxyethyl)carbamate obtained in step 2 (7.4 g, 0.0254 mol) (RT for 12 h). Title compound was obtained as a pale yellow gummy liquid (7.1 g, 86%). 1H NMR (DMSO-d6, 400 MHz) δ 9.59 (s, 1H), 7.52-7.54 (m, 2H), 7.30-7.34 (m, 1H), 7.19-7.21 (m, 1H), 5.75 (s, 2H), 4.40 (s, 2H), 3.37-3.40 (m, 2H), 3.21-3.30 (m, 5H), 1.32-1.41 (m, 9H). LC/MS (Method A): 324.0 (M+H)+. HPLC (Method B) Rt 5.23 min (Purity: 96.2%).
Workup
- customTitle compound was prepared
Sources & evidence
- ORD record
- ord-327c4a91a4994712a157e2d6d0c2506f
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
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