Trifluoroacetic acid → (4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4S)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one

Step L (6): (4S,5S)-4-(3,5-Difluorobenzyl)-5-(morpholin-3-yl)oxazolidin-2-one. A solution of tert-butyl 3-((4S,5S)-4-(3,5-difluorobenzyl)-2-oxooxazolidin-5-yl)morpholine-4-carboxylate (step L (5), 230 mg) in CH2Cl2 (4 mL) was treated with TFA (3 mL). This reaction mixture was stirred at rt for 1.5 h. The mixture was then concentrated in vacuo. Diethyl ether (50 mL) was added and the mixture was washed with 1N HCl solution (40 mL) twice. Aqueous layer was neutralized with 50% aqueous NaOH to pH=12. The mixture was extracted with ethyl acetate (80 mL) twice. The combined organic layers were dried (Na2SO4), and concentrated in vacuo to give 180 mg of the title compound: MS (ESI) (M+H)+ 299.17.

1. concentrationThe mixture was then concentrated in vacuo
2. additionDiethyl ether (50 mL) was added
3. washthe mixture was washed with 1N HCl solution (40 mL) twice
4. extractionThe mixture was extracted with ethyl acetate (80 mL) twice
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. concentrationconcentrated in vacuo

ORD 기록

ord-0eaa60f1c4e14c3cb3fe9b641d351c60

출처 데이터셋

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07388007B2