Tetrahydrofuran → HCID 69159093, compound

HRID 861022Notes

Reaction equation

HRID 861022 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH:16]([CH3:17])[CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:14][C:13]2=[O:24])=[O:11])=[CH:4][CH:3]=1.[CH2:25]1COCC1>CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:25][CH:9]2[C:10]([N:12]2[C@@H:16]([CH3:17])[C@H:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:14][C:13]2=[O:24])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 69375520HCID 69375520, compound

Product 1

HCID 69159093HCID 69159093, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

To a solution of E-3-[3-(4-Bromo-phenyl)-acryloyl]4-methyl-5-phenyl-oxazolidin-2-one from Step 5 and Pd(OAc)2 (0.05 eq.) in THF (0.2M) was added portionwise CH2N2 until the reaction was completed. NMR of aliquots monitored the reaction. The resulting mixture was concentrated and flash chromatography (Hex:EtOAc; 3:2) to afford the two separate diastereoisomers. Each diastereoisomers were submitted to the procedures described in Step 2 and Step 3 to afford the (+) and (−) enantiomers of EXAMPLE 42

Workup

  1. customthe reaction
  2. concentrationThe resulting mixture was concentrated
  3. customflash chromatography (Hex:EtOAc; 3:2) to afford the two
  4. customseparate diastereoisomers
  5. customto afford the (+) and (−) enantiomers of EXAMPLE 42

Sources & evidence

ORD record
ord-a14ff7d54cf04df7ad7e76234bd5e86e
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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