Triethylamine → HCID 57325368, compound

HRID 1957349Notes

Reaction equation

HRID 1957349 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(C)(C)C.C(N(CC)CC)C.C([Li])CCC.[CH3:37][C@H:38]1[C@@H:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:41][C:40](=[O:49])[NH:39]1.C(OC(=O)C(C)(C)C)(=O)C(C)(C)C>C1COCC1>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]([N:39]2[C@@H:38]([CH3:37])[C@@H:42]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:41][C:40]2=[O:49])=[O:17])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 15234Pivalic anhydrideHCID 62493Pivaloyl chlorideHCID 2390774-Phenoxyphenylacetic acidHCID 8531614-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)-HCID 178418339Butyllithium

Product 1

HCID 57325368HCID 57325368, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution containing 4-phenoxyphenylacetic acid (10.0 g, 43.8 mmol) in THF (62.6 mL) at -78° C. was added pivaloyl chloride (5.49 g, 45.6 mmol) followed by triethylamine (4.61 g, 45.6 mmol). The mixture was stirred at -78° C. for 15 minutes, at 0° C. for 1 hour, and then recooled to -78° C. In a separate flask, 2.5M n-butyllithium (20 mL, 50 mmol) was added to a solution of (4S,5R)-(-)-4-methyl-5-phenyl-2-oxazolidinone (8.86 g, 50 mmol) in THF (100 mL) at -78° C. This mixture was stirred for 15 minutes and then transferred to the flask containing pivalic anhydride via cannula. The mixture was stirred for 15 minutes at -78° C. then at room temperature for 18 hours. The solvent was removed, and the residue was partitioned between diethyl ether (500 mL) and 1N HCl (500 mL). The organic layer was dried (MgSO4), filtered and concentrated to provide a light yellow solid. The solid was chromatographed with 10% ethyl acetate in hexane to yield 10.9 g (64%) of the title compound as a white solid.

Workup

  1. customrecooled to -78° C
  2. stirringThis mixture was stirred for 15 minutes
  3. stirringThe mixture was stirred for 15 minutes at -78° C.
  4. waitat room temperature for 18 hours
  5. customThe solvent was removed
  6. customthe residue was partitioned between diethyl ether (500 mL) and 1N HCl (500 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto provide a light yellow solid
  11. customThe solid was chromatographed with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-44db5790bdc54124ac8f1ac3a24f06f0
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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