3-Carboxyphenylboronic acid → HCID 86680669, compound

HRID 1615432Notes

Reaction equation

HRID 1615432 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:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37]([OH:39])=[O:38])(O)O>>[C:27]([O:26][C:24]([N:19]1[C:18]([C:34]2[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=2)[C:37]([OH:39])=[O:38])=[CH:23][O:22][CH2:21][CH2:20]1)=[O:25])([CH3:28])([CH3:29])[CH3:30]

Participants

3

Reactant 2

HCID 27339573-Carboxyphenylboronic acidHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680669HCID 86680669, compoundYield 26%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and 3-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 (26% yield); 1H-NMR (d6-DMSO) 1.01 (9H, s), 3.71 (2H, t), 4.12 (2H, t), 6.50 (1H, s), 7.40-7.46 (2H, m), 7.74-7.77 (2H, m), 12.94 (1H, brs); 13C-NMR (d6-DMSO) 27.7, 41.5, 66.8, 126.8, 128.0, 128.2, 130.1, 133.0; MS ES(+) 249.9 (M+-tBu). IR λmax=1694 cm−1.

Sources & evidence

ORD record
ord-d98397baae21413d99011052217d49a0
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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