1-Hydroxybenzotriazole → tert-Butyl {2-[({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamate

To a solution of the carboxylic acid (6b, 1.34 g, 4.87 mmol) of Example 9 or 16 in methylene chloride (35 mL) were added triethylamine (2.71 mL), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.41 g), 1-hydroxybenzotriazole.monohydrate (1.15 g), and tert-butyl 2-(aminooxy)ethylcarbamate (1.12 g) described in Reference Example 9, followed by agitating at room temperature overnight. To the residue resulting from concentrating the reaction solution under reduced pressure was added water, followed by extracting with ethyl acetate. The resulting organic layer was washed with 0.1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, filtrated, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=8/2-0/10) to afford 1.77 g of the title compound (yield 84%).

1. customTo the residue resulting
2. concentrationfrom concentrating the reaction solution under reduced pressure
3. additionwas added water
4. extractionby extracting with ethyl acetate
5. washThe resulting organic layer was washed with 0.1M hydrochloric acid, saturated sodium bicarbonate aqueous solution
6. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate
7. filtrationfiltrated
8. concentrationconcentrated
9. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=8/2-0/10)

ORDレコード

ord-4c45c79841144269a8c276b5b17ba6e7

出典データセット

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09181250B2