4-Nitrobenzoic Acid → HCID 178486949, compound

To a solution of triphenylphosphine (142.7 mg, 0.546 mmol) in tetrahydrofuran (2 mL) was added diisopropyl azodicarboxylate (11 mg, 0.54 mmol), and the resulting mixture was stirred at room temperature for 30 min. The mixture was cooled to −50° C. and cis-3-(4-bromo-2-methoxyphenyl)cyclobutanol (100 mg, 0.389 mmol) in tetrahydrofuran (0.5 mL) was added. The reaction was stirred for 20 min, followed by addition of solid 4-nitrobenzoic acid (90.97 mg, 0.546 mmol), the resulting mixture was warmed to room temperature and allowed to stir at room temperature for 15 hr. The reaction was then cooled to 0° C., to which was added sodium hydroxide (5 mL, 0.5M in methanol). After 40 min the reaction was quenched with sat. ammonium chloride (5 mL), and diluted with ethyl acetate (15 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated to dryness to give the title compound (78 mg, 54%) as an oil.

1. temperatureThe mixture was cooled to −50° C.
2. stirringThe reaction was stirred for 20 min
3. temperaturethe resulting mixture was warmed to room temperature
4. stirringto stir at room temperature for 15 hr
5. temperatureThe reaction was then cooled to 0° C., to which
6. customAfter 40 min the reaction was quenched with sat. ammonium chloride (5 mL)
7. additiondiluted with ethyl acetate (15 mL)
8. customThe organic layer was separated
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. customevaporated to dryness

ORD record

ord-9ac86dcda32643e89b02494e696623f9

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889730B2