Formic Acid → HCID 9904426, compound

Temperature

50 °C

A mixture of formic acid (0.011 mL, 0.29 mmol) and acetic anhydride (0.026 mL, 0.28 mmol) was heated to 50° C. for 1 h. To this mixture at room temperature was added a mixture of [(3S,4R)-3-(benzyloxyaminomethyl)-1-(5-benzyloxypentyl)-4-butyl-pyrrolidin-2-one (65 mg, 0.14 mmol) and triethylamine (0.02 mL, 0.18 mmol) in methylene chloride (3 mL). The resulting mixture was stirred at room temperature for 30 minutes. The reaction was diluted with methylene chloride (5 mL) and quenched with water (5 mL). The organic phase was washed with brine (5 mL), dried (Na2SO4), filtered, and concentrated. The residue was dissolved in methanol (3 mL) and stirred under a hydrogen balloon in the presence of palladium on activated carbon (40 mg) for 4 h. The reaction mixture was filtered, concentrated, and the residue was purified by HPLC to afford 25 mg (58%) of N-[(3S,4R)-4-butyl-1-(5-hydroxypentyl)-2-oxopyrrolidin-3-yl-methyl]-N-hydroxyformamide as a colorless glass: 1H NMR (CD3OD) δ 8.33 (s, 0.5 H), 7.98 (s, 0.5 H), 3.80 (m, 1 H), 3.57 (m, 3 H), 3.33 (m, 3 H), 3.07 (t, 1H), 2.55 (m, 1 H), 2.12-2.26 (m, 1H), 1.33-1.71 (m, 12 H), 0.94 (t, 3 H). MS(ES) m/e 301 [M+H]+.

1. additionTo this mixture at room temperature was added
2. customquenched with water (5 mL)
3. washThe organic phase was washed with brine (5 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in methanol (3 mL)
8. stirringstirred under a hydrogen balloon in the presence of palladium on activated carbon (40 mg) for 4 h
9. filtrationThe reaction mixture was filtered
10. concentrationconcentrated
11. customthe residue was purified by HPLC

ORD record

ord-4ff680e591814cd48ea173d1b37c454e

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456211B2