Chlorotrimethylsilane → (S)-4-benzyl-3-((2R,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propanoyl)oxazolidin-2-one

HRID 2172817Notes

Reaction equation

HRID 2172817 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:17])[CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg+2].[Cl-].[Cl-].[Br:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=[O:26].Cl[Si:31]([CH3:34])([CH3:33])[CH3:32]>CCOC(C)=O.CCN(CC)CC>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:17])[C@H:15]([CH3:16])[C@@H:25]([C:24]1[CH:27]=[CH:28][CH:29]=[C:22]([Br:21])[CH:23]=1)[O:26][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 765833-BromobenzaldehydeHCID 2733696(4S)-4-Benzyl-3-propanoyl-1,3-oxazolidin-2-oneHCID 5360315Magnesium Chloride

Product 1

HCID 66743729(S)-4-benzyl-3-((2R,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propanoyl)oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (S)-4-benzyl-3-propionyloxazolidin-2-one, anhydrous MgCl2 (0.104 g, 1.09 mmol) and 3-bromobenzaldehyde in EtOAc is added Et3N followed by chlorotrimethylsilane. The reaction mixture is stirred under argon at room temperature for 24 h and then filtered through a layer of a silica gel, washing with EtOAc. The combined filtrates are concentrated under reduced pressure and the residue is purified by flash chromatography (1 to 30% EtOAc/hexane gradient) to give (S)-4-benzyl-3-((2R,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propanoyl)oxazolidin-2-one.

Workup

  1. filtrationfiltered through a layer of a silica gel
  2. washwashing with EtOAc
  3. concentrationThe combined filtrates are concentrated under reduced pressure
  4. customthe residue is purified by flash chromatography (1 to 30% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-952744ef1f0c4ade82eb97d8c502e7e5
Source dataset
uspto-grants-2015_06
Patent number
US09056849B2

Reaction notes

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