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

HRID 1615425Notes

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

Participants

Reactant 2

HCID 66827Phenylboronic Acid

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

Product 1

HCID 86680663tert-butyl 5-phenyl-2H-1,4-oxazine-4(3H)-carboxylateYield 56%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and phenylboronic acid using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as a white solid (56% yield); 1H-NMR (d6-DMSO) 1.04 (9H, s), 3.68 (2H, m), 4.09 (2H, m), 6.38 (1H, s), 7.18-7.20 (3H, m), 7.27-7.29 (2H, m); 13C-NMR (CDCl3) 27.7, 41.5, 66.8, 125.0, 126.3, 128.0, 132.2; MS ES(+) 206.0 (M+-tBu); HRMS m/z calcd for C15H19NO3+H+ 262.1443 [M+H+]. Found 262.1447. IR λmax=3441, 1701, 1367, 1355, 1163 cm−1.

Sources & evidence

ORD record: ord-149e1f7e9b984bb69ce4ae1b9af52d01
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765751B2

Reaction notes

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