Allyl bromide → 3-(Allyl-benzyloxycarbonyl-amino)-5-oxazol-2-yl-benzoic acid methyl ester

HRID 1664212Notes

Reaction equation

HRID 1664212 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[C:6]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH:5]=1.[H-].[Na+].[CH2:29](Br)[CH:30]=[CH2:31]>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[C:6]([N:15]([CH2:31][CH:30]=[CH2:29])[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH:5]=1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 674415993-Benzyloxycarbonylamino-5-oxazol-2-yl-benzoic acid methyl ester

Product 1

HCID 674411643-(Allyl-benzyloxycarbonyl-amino)-5-oxazol-2-yl-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Benzyloxycarbonylamino-5-oxazol-2-yl-benzoic acid methyl ester (330 mg, 0.927 mmol, I eq) is dissolved in THF (10 ml). NaH (48 mg, 60%,1.21 mmol, 1.3 eq) is added in portions, and the reaction mixture is stirred for 30 min at rt. TBAI (35 mg, 92.7 μmol, 0.1 eq) and allyl bromide (119 μl, 1.39 mmol, 1.5 eq) are added, and the reaction mixture is stirred for 20 h and then quenched with HCl (1N in H2O). The aqueous phase is extracted with EtOAc. The organic layer is washed with brine, dried over sodium sulfate, filtered and concentrated to give the product.

Workup

  1. stirringthe reaction mixture is stirred for 20 h
  2. customquenched with HCl (1N in H2O)
  3. extractionThe aqueous phase is extracted with EtOAc
  4. washThe organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the product

Sources & evidence

ORD record
ord-365c1979b09343cbae79eaf71106b36d
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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