4-Hydroxyphenylboronic acid → HCID 86680666, compound

HRID 1615429Notes

Reaction equation

HRID 1615429 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:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>>[OH:31][C:32]1[CH:37]=[CH:36][C:35]([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:34][CH:33]=1

Participants

3

Reactant 2

HCID 27343604-Hydroxyphenylboronic acidHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680666HCID 86680666, compoundYield 44%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and 4-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 (44% yield); 1H-NMR (d6-DMSO) 1.37 (9H, s), 3.65 (2H, t), 4.05 (2H, t), 6.20 (1H, s), 6.68 (2H, d), 7.00 (2H, d), 9.25 (1H, s); 13C-NMR (CDCl3) 27.7, 41.7, 66.8, 114.7, 126.4, 131.4); MS ES(+) 222.1 (M+-tBu); Anal. Calcd for C15H19NO4: C, 64.97; H, 6.91; N, 5.05. Found: C, 64.59; H, 7.05; N, 4.85. IR λmax=3402, 1672 cm−1.

Sources & evidence

ORD record
ord-f749a179fbe4427c941e487d2f0c2ad8
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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