Ammonium Chloride → (R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone

온도

-30 °C

N-Methoxy-N-methyl-(R)-5-(Benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-pentanamide (305) (10 g, 24 mmol) was dissolved in THF (250 mL) and the solution was cooled to −30° C. in a dry-ice acetone bath. MeMgBr (3M in Et2O, 123 mL, 369 mmol) was added drop-wise over 30 minutes. The bath temperature was slowly allowed to increase to 0° C. and then was maintained at 0° C. until TLC showed no further reaction progress (˜80-90% complete). Saturated NH4Cl (aq) was then slowly added to the reaction mixture at 0° C. and the THF was removed under reduced pressure. The resulting aqueous solution was then extracted with EtOAc and the extracts were washed with water and then brine. The residue was then purified by column chromatography (EtOAc/hexanes) to give (R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone (306), (6.5 g, 18 mmol, 75% yield).

1. temperatureto increase to 0° C.
2. temperaturewas maintained at 0° C. until TLC
3. customthe THF was removed under reduced pressure
4. extractionThe resulting aqueous solution was then extracted with EtOAc
5. washthe extracts were washed with water
6. customThe residue was then purified by column chromatography (EtOAc/hexanes)

ORD 기록

ord-96670990d15e4bcc90f8296974acea66

출처 데이터셋

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09382246B2