Benzyl azide → HCID 67530374, compound

HRID 2388238Notes

Reaction equation

HRID 2388238 reaction equation
[C:1]([C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][O:11][C:7]=2[C:6]([OH:18])=[C:5]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:4]=1)#[CH:2].[CH2:24]([N:31]=[N+:32]=[N-:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(Cl)Cl.O>[CH2:24]([N:31]1[CH:2]=[C:1]([C:3]2[C:8]3[C:9]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[N:10][O:11][C:7]=3[C:6]([OH:18])=[C:5]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:4]=2)[N:33]=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 12152Benzyl azide2×HCID 23667548Sodium AscorbateHCID 86648129HCID 86648129, compound

Product 1

HCID 67530374HCID 67530374, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 4-ethynyl-7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (185 mg, 0.60 mmol), benzyl azide (0.087 mL, 0.66 mmol), CuSO4-5H2O (7.5 mg, 0.03 mmol), and sodium ascorbate (18 mg, 0.09 mmol) were added to a mixture of CH2Cl2 (2 mL) and water (2 mL). The mixture was stirred at room temperature for 16 h. Another equiv. of benzyl azide was added, and the mixture was stirred for an additional 16 h. The mixture was diluted with CH2Cl2 (20 mL) and water (20 mL). The aqueous layer was extracted with additional CH2Cl2 and the combined organic layer was dried over MgSO4 and concentrated. The crude product was purified twice by flash chromatography (first with 0-100% EtOAc/hexanes, then with 0-50% CH2Cl2/EtOAc) to afford 100 mg of the title compound. MS: (+) m/z 442.33 (M+1).

Workup

  1. stirringthe mixture was stirred for an additional 16 h
  2. extractionThe aqueous layer was extracted with additional CH2Cl2
  3. dry with materialthe combined organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified twice by flash chromatography (first with 0-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-b536c05836a34b609ce5503187b9dda0
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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