Trifluoroacetic acid → 3-(trans-1-benzyl-4-phenyl-3-pyrrolidinylcarbonyl)-4-(S)-phenyl-2-oxazolidinone

HRID 1378467

Reaction equation

HRID 1378467 reaction equation
[C:1]([N:11]1[C@@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][O:13][C:12]1=[O:22])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:23]([N:30]([CH2:34][Si](C)(C)C)[CH2:31]OC)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:23]([N:30]1[CH2:34][C@@H:3]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@H:2]([C:1]([N:11]2[C@@H:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:14][O:13][C:12]2=[O:22])=[O:10])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 679769(4S)-4-Phenyl-3-(3-phenylprop-2-enoyl)-1,3-oxazolidin-2-one

Product 1

HCID 677115143-(trans-1-benzyl-4-phenyl-3-pyrrolidinylcarbonyl)-4-(S)-phenyl-2-oxazolidinone

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound from step 8b (294 mg, 1.2 mmol) was dissolved in toluene (10 mL), and the solution flushed with N2. N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine (284 mg, 0.227 mmol) was added, the mixture was stirred for 20 minutes and trifluoroacetic acid (1M, 0.1 mL, 0.10 mmol) was added dropwise. The mixture was stirred for 1.5 hour at room temperature, then diluted with 50 mL of ethyl acetate, washed with 5% aqueous NaHCO3 and dried over Na2SO4. The solvent was removed and the residue was dried under vacuum (542 mg). The isomers were separated by chromatography on silica gel, and the major isomer (3R,4R) was taken to the next step. MS m/z 427 (M+H)+.

Workup

  1. customthe solution flushed with N2
  2. stirringThe mixture was stirred for 1.5 hour at room temperature
  3. washwashed with 5% aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe residue was dried under vacuum (542 mg)
  7. customThe isomers were separated by chromatography on silica gel

Sources & evidence

ORD record
ord-bba1c7337734463eb39191ac178f3edf
Source dataset
uspto-grants-1997_09
Patent number
US05668164

Linked notes

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