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

HRID 1665982노트

반응식

HRID 1665982 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-4e182a9096024c4788f1565aef77b12e
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039674B2

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