4-Carboxyphenylboronic Acid → 4-(4-(tert-butoxycarbonyl)-3,4-dihydro-2H-1,4-oxazin-5-yl)benzoic acid
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.B([C:34]1[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=1)(O)O>>[C:27]([O:26][C:24]([N:19]1[C:18]([C:34]2[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=2)=[CH:23][O:22][CH2:21][CH2:20]1)=[O:25])([CH3:28])([CH3:29])[CH3:30]Participants
3
Procedure
This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and 4-boronobenzoic acid using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as an off-white solid (30% yield); 1H-NMR (d6-DMSO) 1.06 (9H, s), 3.69 (2H, t), 4.12 (2H, t), 6.58 (1H, s), 7.29 (2H, d), 7.85 (2H, d), 12.83 (1H, brs); 13C-NMR (CDCl3); 27.7, 41.3, 66.8, 124.5, 130.1, 134.0; MS ES(+) 249.9 (M+-tBu). IR λmax=1701, 1674 cm−1.
Sources & evidence
- ORD record
- ord-54776ad5a43645daaa804268d01c69d8
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765751B2
Reaction notes
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