Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86625210, compound

1.01 g of Z-SAR-OH (available from Kokusan Chemical Co., Ltd.), 4.72 mL of diisopropylethylamine, 1.83 g of 1-hydroxybenzotriazole monohydrate, and 1.32 g of N,O-dimethyl hydroxylamine hydrochloride were dissolved in 15 mL of N,N-dimethylformamide, then 2.6 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added thereto under an ice-cold condition, and the mixture was stirred for 2.5 hours at room temperature. To the reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate, and the solution was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1), to obtain 1.02 g of benzyl{2-[methoxy(methyl)amino]-2-oxoethyl}methylcarbamate [2-1] (hereinafter, referred to as the compound [2-1]) as a pale yellow oily product.

1. extractionthe solution was extracted with ethyl acetate
2. washThe resulting organic layer was washed with saturated brine
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationThe insolubles were filtered
5. concentrationthe filtrate was concentrated under reduced pressure
6. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)

ORD record

ord-ebeb14c3fed346c48efb367dce22f321

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977336B2