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

HRID 1665982Notes

Reaction equation

HRID 1665982 reaction equation
[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

Participants

6

Reactant 5

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4e182a9096024c4788f1565aef77b12e
Source dataset
uspto-grants-2011_10
Patent number
US08039674B2

Reaction notes

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