4-Benzoylbenzeneboronic acid → HCID 86680674, compound

HRID 1615437Notes

Reaction equation

HRID 1615437 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.[C:31]([C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[C:31]([C:39]1[CH:44]=[CH:43][C:42]([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:41][CH:40]=1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 41972354-Benzoylbenzeneboronic acidHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680674HCID 86680674, compoundYield 65%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and 4-benzoylphenylboronic acid using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as a white solid (65% yield); 1H-NMR (d6-DMSO) 1.11 (9H, s), 3.71 (2H, t), 4.15 (2H, t), 6.65 (1H, s), 7.37-7.39 (2H, m), 7.57-7.59 (2H, m), 7.68-7.71 (5H, m); MS ES(+) 366.2 (M++1); Anal. Calcd for C22H23NO4: C, 72.31; H, 6.34; N, 3.83. Found: C, 71.95; H, 6.24; N, 9.98. IR λmax=1695, 1645, 1604, 1360 cm−1.

Sources & evidence

ORD record
ord-2d915ef19ac548d384b69c9f4219f338
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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