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

HRID 539087ノート

反応式

HRID 539087 の反応式
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

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 8471TriethylamineHCID 57466763Triphosph-1-eneHCID 67034313(R)-2-amino-2-(2,4-difluorophenyl)ethanol hydrochloride

生成物 1

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

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-0c459ff9b9324640ac9062f82abb4cee
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

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