Hydrochloric Acid → HCID 22718546, compound

HRID 1582610Notes

Reaction equation

HRID 1582610 reaction equation
C([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([Br:21])=[C:16]([CH2:17][CH2:18][CH2:19][NH2:20])[C:11]=2[O:10][CH:9]1[CH2:22][CH3:23])=O)(C)(C)C.Cl.[CH2:25](Cl)Cl>O1CCOCC1>[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([Br:21])=[C:16]([CH2:17][CH2:18][CH2:19][NH2:20])[C:11]=2[O:10][CH:9]1[CH2:22][CH3:23])(=[O:5])[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 22718666HCID 22718666, compound

Product 1

HCID 22718546HCID 22718546, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-t-butoxycarbonyl 7-(3-aminopropyl)-6-bromo-2-ethylbenzoxazole (30 mg, 0.078 mmol), in methylene chloride (1 mL) was treated with 4 M HCl in dioxane (1 mL) and stirred for 2 hours. The solvent was evaporated and the residue was taken up in pyridine (2 mL) and treated with acetic anhydride (100 μL). After stirring for 2 hours, the reaction was diluted with EtOAc (5 mL) and washed with saturated aqueous copper (II) sulfate (2×5 mL). The organic layer was dried with magnesium sulfate and evaporated. The product was purified on a silica gel column and eluted with 25% EtOAc/hexanes to give a clear oil (10 mg, 40%).

Workup

  1. customThe solvent was evaporated
  2. additiontreated with acetic anhydride (100 μL)
  3. stirringAfter stirring for 2 hours
  4. additionthe reaction was diluted with EtOAc (5 mL)
  5. washwashed with saturated aqueous copper (II) sulfate (2×5 mL)
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. customevaporated
  8. customThe product was purified on a silica gel column
  9. washeluted with 25% EtOAc/hexanes

Sources & evidence

ORD record
ord-dbf7768b9163437ea55595f84eb8b151
Source dataset
uspto-grants-2004_05
Patent number
US06737431B2

Reaction notes

Loading…