Tetrahydrofuran → (4R)-4-benzyl-3-[(2S)-3-(4-chlorophenyl)-2-methylpropanoyl]-1,3-oxazolidin-2-one

HRID 243819ノート

反応式

HRID 243819 の反応式
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])N1C(=O)CC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].Cl[CH:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl-:37].[NH4+:38].[O:39]1C[CH2:42][CH2:41][CH2:40]1>>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:38]1[C:40](=[O:39])[C@@H:41]([CH3:42])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:37])=[CH:32][CH:31]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 5

HCID 8028Tetrahydrofuran2 回HCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10966403(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinoneHCID 11805852Chlorobenzyl bromide

生成物 1

HCID 66689991(4R)-4-benzyl-3-[(2S)-3-(4-chlorophenyl)-2-methylpropanoyl]-1,3-oxazolidin-2-one

実験手順

To a solution of the compound (10 g) prepared in Example 16 in tetrahydrofuran (80 mL), a solution of sodium hexamethyldisilazide in tetrahydrofuran (1M, 49.3 mL) was dropped at −78° C., followed by stirring for 1 hour. Then, chlorobenzyl bromide (10.6 g) was dropped thereto, followed by stirring at −78° C. for 7 hours. The reaction mixture was added with a saturated aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. Then, the obtained solid was washed with hexane to thereby give the title compound (12.8 g) having the following physical properties.

後処理

  1. stirringby stirring at −78° C. for 7 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. washThen, the obtained solid was washed with hexane

出典と根拠

ORDレコード
ord-9ca9991345484e66a28701f0d8109cbd
出典データセット
uspto-grants-2014_02
特許番号
US08653305B2

反応ノート

読み込み中…