4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide → HCID 86680670, compound
Reaction equation
O(P(O[C:18]1[N:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:21][O:22][CH:23]=1)(OC1C=CC=CC=1)=O)C1C=CC=CC=1.CC1(C)C(C)(C)OB([C:39]2[CH:44]=[CH:43][C:42]([NH:45][C:46](=[O:48])[CH3:47])=[CH:41][CH:40]=2)O1>>[C:46]([NH:45][C:42]1[CH:43]=[CH:44][C:39]([C:18]2[N:19]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:21][O:22][CH:23]=2)=[CH:40][CH:41]=1)(=[O:48])[CH3:47]Participants
3
Procedure
This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as a white solid (44% yield); 1H-NMR (d6-DMSO) 1.07 (9H, s), 2.02 (3H, s), 3.66 (2H, t), 4.08 (2H, t), 6.32 (1H, s), 7.09 (2H, d), 7.49 (2H, d), 9.88 (1H, s); MS ES(+) 263.0 (M+-tBu); HRMS m/z calcd for C17H22N2O4+H+ 319.1658 [M+H+]. Found 319.1658. IR λmax=1694 cm−1.
Sources & evidence
- ORD record
- ord-bac0fa9e20d745a5b5d3d1cb8c57f08b
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765751B2
Reaction notes
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