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

HRID 243819노트

반응식

HRID 243819 반응식
[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

참가 물질

6

반응물 5

HCID 8028Tetrahydrofuran2회HCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10966403(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinoneHCID 11805852Chlorobenzyl bromide

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ca9991345484e66a28701f0d8109cbd
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653305B2

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