Phenylacetic Acid → HCID 11066354, compound

HRID 1957347Notes

Reaction equation

HRID 1957347 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(C)(C)C.[Li]CCCC.[CH3:23][C@H:24]1[C@@H:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:27][C:26](=[O:35])[NH:25]1.C(OC(=O)C(C)(C)C)(=O)C(C)(C)C>C1COCC1.C(N(CC)CC)C>[C:1]1([CH2:7][C:8]([N:25]2[C@@H:24]([CH3:23])[C@@H:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:27][C:26]2=[O:35])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 999Phenylacetic AcidHCID 15234Pivalic anhydrideHCID 62493Pivaloyl chlorideHCID 8531614-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)-HCID 178418339Butyllithium

Product 1

HCID 11066354HCID 11066354, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A mechanically stirred solution of phenylacetic acid at -78° C. is treated with one part pivaloyl chloride then one part triethylamine. The mixture is stirred at -78° C. for 15 minutes, at 0° C. for 45 minutes, then recooled to -78° C. In a separate flask, one part 2.5M nBuLi is added to a solution of (4S,5R)-(-)-4-methyl-5-phenyl-2-oxazolidinone in THF at -78° C. The solution is stirred for 15 minutes then transferred to the flask containing pivalic anhydride via cannula. The mixture is stirred for 15 minutes at -78° C. and 9 hours at room temperature. The mixture is quenched with 2M KHSO4 and, after evaporation of the THF, is extracted 3 times with ethyl acetate. The combined ethyl acetate extracts are dried over MgSO4, filtered and concentrated to provide the crude title compound which is purified by column chromatography eluting with ethyl acetate-hexane.

Workup

  1. customrecooled to -78° C
  2. stirringThe solution is stirred for 15 minutes
  3. stirringThe mixture is stirred for 15 minutes at -78° C. and 9 hours at room temperature
  4. customThe mixture is quenched with 2M KHSO4
  5. customafter evaporation of the THF
  6. extractionis extracted 3 times with ethyl acetate
  7. dry with materialThe combined ethyl acetate extracts are dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d5ecb82c815b4098932e2da89d32a011
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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