N-bromobutanimide → HCID 54126761, compound

HRID 1369270Notes

Reaction equation

HRID 1369270 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[NH:5][C:6](=[O:8])[CH3:7].C1C(=O)N([Br:25])C(=O)C1>C1COCC1.S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH:5][C:6](=[O:8])[CH3:7])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[C:14]([Br:25])[CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 720747Ac-Tyr-OMe H2O

Product 1

HCID 54126761HCID 54126761, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To N-acetyl-L-tyrosine methyl ester (6 g, 25.3 mmol) in THF (60 mL) at rt was added NBS (5.4 g, 30.3 mmol) followed by five drops of sulfuric acid. The mixture was stirred for 16 h at rt The solvent was removed under reduced pressure and then water was added. The aqueous layer was extracted twice with EtOAc, and the combined extracts were dried over magnesium sulfate and concentrated to a solid. The solid was recrystallized from ethyl acetate/hexane (6 g, 75%). MS (M+H]+ 316.

Workup

  1. customwas removed under reduced pressure
  2. additionwater was added
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. dry with materialthe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated to a solid
  6. customThe solid was recrystallized from ethyl acetate/hexane (6 g, 75%)

Sources & evidence

ORD record
ord-72e9d614001840ad84ecf2501a867ae9
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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