Trifluoroacetic acid → (4S)-3-[3-(3-carboxy-4-methoxyphenyl)-2-ethylpropionyl]-4-benzyl-2-oxazolidinone

HRID 1634530Notes

Reaction equation

HRID 1634530 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:19](O)[CH:20]([CH2:36][CH3:37])[C:21]([N:23]2[C@@H:27]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:26][O:25][C:24]2=[O:35])=[O:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])=[O:10])C1C=CC=CC=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[C:9]([C:11]1[CH:12]=[C:13]([CH2:19][CH:20]([CH2:36][CH3:37])[C:21]([N:23]2[C@@H:27]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:26][O:25][C:24]2=[O:35])=[O:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])([OH:10])=[O:8]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69758110(4S)-3-[3-(3-benzyloxycarbonyl-4-methoxyphenyl)-2-ethyl-3-hydroxypropionyl]-4-benzyl-2-oxazolidinone

Product 1

HCID 69758575(4S)-3-[3-(3-carboxy-4-methoxyphenyl)-2-ethylpropionyl]-4-benzyl-2-oxazolidinoneYield 124.8%

Procedure

Next, (4S)-3-[3-(3-benzyloxycarbonyl-4-methoxyphenyl)-2-ethyl-3-hydroxypropionyl]-4-benzyl-2-oxazolidinone (1.35 g, 2.61 mmol) and 22 ml of trifluoroacetic acid were mixed under cooling with ice and triethylsilane (3.95 ml, 26.1 mmol) was added over 5 minutes. The mixture was stirred for 1 hour under cooling with ice, followed by stirring for 4 days at room temperature. The reaction mixture was concentrated and the residue was poured into 0.5 mol/l aqueous solution of sodium hydroxide, which was washed with ethyl acetate. The aqueous layer was made acidic and extracted with methylene chloride. The extract was washed with brine, then dried over anhydrous magnesium sulfate and concentrated to obtain 1.34 g of crude (4S)-3-[3-(3-carboxy-4-methoxyphenyl)-2-ethylpropionyl]-4-benzyl-2-oxazolidinone as a yellow oil. This compound was used for next reaction without purifying further.

Workup

  1. additionwas added over 5 minutes
  2. temperatureunder cooling with ice
  3. stirringby stirring for 4 days at room temperature
  4. concentrationThe reaction mixture was concentrated
  5. additionthe residue was poured into 0.5 mol/l aqueous solution of sodium hydroxide, which
  6. washwas washed with ethyl acetate
  7. extractionextracted with methylene chloride
  8. washThe extract was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a5a29a36fe774fb5bb26c53285c7eb16
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

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