(3-hydroxyphenyl)boronic Acid → tert-butyl 5-(3-hydroxyphenyl)-2H-1,4-oxazine-4(3H)-carboxylate

HRID 1615430Notes

Reaction equation

HRID 1615430 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.[OH:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1>>[OH:31][C:32]1[CH:37]=[C:36]([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:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 2734359(3-hydroxyphenyl)boronic AcidHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680667tert-butyl 5-(3-hydroxyphenyl)-2H-1,4-oxazine-4(3H)-carboxylateYield 35%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and 3-hydroxyphenylboronic acid using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as an off-white solid (35% yield); 1H-NMR (d6-DMSO) 1.08 (9H, s), 3.65 (2H, t), 4.07 (2H, t), 6.34 (1H, s), 6.58-6.63 (3H, m), 7.06 (1H, m), 9.23 (1H, s); MS ES(+) 222.1 (M+-tBu); Anal. Calcd for C15H19NO4: C, 64.97; H, 6.91; N, 5.05. Found: C, 64.77; H, 7.08; N, 4.85. IR λmax=3365, 1666 cm−1.

Sources & evidence

ORD record
ord-661443ab9be244ec8b8c8d27e21893e6
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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