Sodium Bicarbonate → HCID 69216999, compound

HRID 1296515Notes

Reaction equation

[CH2:1]([C:3]1([CH2:18][CH3:19])[C:8]2[CH:9]=[C:10](B(O)O)[CH:11]=[CH:12][C:7]=2[N:6]([CH3:16])[C:5](=[O:17])[O:4]1)[CH3:2].C(=O)(O)[O-:21].[Na+].OOS([O-])=O.[K+].S(=O)(O)[O-].[Na+]>O.CC(C)=O>[CH2:1]([C:3]1([CH2:18][CH3:19])[C:8]2[CH:9]=[C:10]([OH:21])[CH:11]=[CH:12][C:7]=2[N:6]([CH3:16])[C:5](=[O:17])[O:4]1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of 4,4-diethyl-1-methyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl boronic acid (3.97 g, 15.09 mmol) in a 15% acetone and 85% water mixture solution (80 mL) was added sodium bicarbonate (3.80 g, 45.27 mmol). The resulting suspension was cooled to 0° C. and Oxone (9.09 g, 14.80 mmol) was added portionwise over 20 minutes. After 45 minutes, sodium bisulfite (4.25 g, 4.10 mmol) was added. The solution was stirred for an additional 10 minutes, diluted with water and extracted several times with ethyl acetate. The organic layers were dried over magnesium sulfate and concentrated. Trituration with ether gave 4,4-diethyl-6-hydroxy-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one as a white solid (2.45 g, 69%). 1H NMR (DMSO-d6): δ 9.32 (s, 2H), 6.90 (d, J=8.8 Hz, 1H), 6.75 (dd, J=8.7, 2.6 Hz, 1H), 6.58 (d, J=2.7 Hz, 1H), 3.22 (s, 3H), 1.99 (m, 4H), 0.79 (t, J=7.3 Hz, 6H). MS (ESI) m/z 236 ([M+H]+); MS (ESI) m/z 234 ([M−H]−); Anal. calcd for C13H17NO3: C, 66.36; H, 7.28; N, 5.95. Found: C, 66.02; H, 7.34; N, 5.74.

Workup

extractionextracted several times with ethyl acetate
dry with materialThe organic layers were dried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-00e87785c8234f7196d8120d86317035
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247625B2

Reaction notes

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