Tetrahydrofuran → (R)-4-(2,4-difluorophenyl)oxazolidin-2-one

HRID 539087노트

반응식

HRID 539087 반응식
Cl.[NH2:2][C@H:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])[CH2:4][OH:5].CCN(CC)CC.P=PP.C1C[O:27][CH2:26]C1>>[F:13][C:7]1[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=1[C@@H:3]1[CH2:4][O:5][C:26](=[O:27])[NH:2]1

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 8471TriethylamineHCID 57466763Triphosph-1-eneHCID 67034313(R)-2-amino-2-(2,4-difluorophenyl)ethanol hydrochloride

생성물 1

HCID 67033164(R)-4-(2,4-difluorophenyl)oxazolidin-2-one수율 91%

실험 절차

To a stirred mixture of (R)-2-amino-2-(2,4-difluorophenyl)ethanol hydrochloride (0.58 g, 2.8 mmol) in THF (18 mL) was added Et3N (1.2 mL, 8.9 mmol). The reaction mixture was cooled in an ice bath under N2. A solution of triphosphene (0.33 g, 1.1 mmol) in THF (10 mL) was added. The reaction was allowed to warm to ambient temperature and stirred for 2 hours. The reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexane, 1:1) to give (R)-4-(2,4-difluorophenyl)oxazolidin-2-one (0.50 g, 91%).

후처리

  1. temperatureThe reaction mixture was cooled in an ice bath under N2
  2. customThe reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (EtOAc/hexane, 1:1)

출처 및 근거

ORD 기록
ord-0c459ff9b9324640ac9062f82abb4cee
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

반응 노트

불러오는 중…