tert-Butanol → 2-Bromo-6-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-fluorobenzoic Acid

HRID 519397Notes

Reaction equation

[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([N:11]2[CH2:22][CH2:21][N:20]3[C:13](=[CH:14][C:15]4[CH2:16][C:17]([CH3:24])([CH3:23])[CH2:18][C:19]=43)[C:12]2=[O:25])[C:3]=1[CH:4]=[O:5].C([OH:30])(C)(C)C.CC(=CC)C.[O-]Cl=O.[Na+]>O.ClCCl>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([N:11]2[CH2:22][CH2:21][N:20]3[C:13](=[CH:14][C:15]4[CH2:16][C:17]([CH3:23])([CH3:24])[CH2:18][C:19]=43)[C:12]2=[O:25])[C:3]=1[C:4]([OH:30])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 2-bromo-6-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-fluorobenzaldehyde 128a (810 mg, 2.0 mmol), tert-butyl alcohol (50 mL), and dichloromethane (3 mL) was added 2-methyl-2-butene (22 mL, 262 mmol). An aqueous solution (20 mL) of NaClO2 (1.8 g, 20.0 mmol) and NaH2PO4 dihydrate (2.2 g, 14.0 mmol) was added dropwise at 0° C. The mixture was stirred at 0° C. for 1 h. It was then treated with water (30 mL) and extracted with ethyl acetate (4×90 mL). The combined organic extract was dried over MgSO4 and concentrated under reduced pressure to afford 129a (930 mg, 84%) as a yellow solid. MS-ESI: [M+H]+ 421.1

Workup

extractionextracted with ethyl acetate (4×90 mL)
extractionThe combined organic extract
dry with materialwas dried over MgSO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d0ef5d02ee87407d8726cb199e5c2a8f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115152B2

Reaction notes

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