Triethylamine → HCID 56997872, compound

HRID 982117Notes

Reaction equation

HRID 982117 reaction equation
CS(Cl)(=O)=O.[N:6]([CH2:9][C@H:10]1[C:15]2[C:16]([CH3:22])=[CH:17][CH:18]=[C:19]([O:20][CH3:21])[C:14]=2[CH2:13][C@@H:12]([CH2:23]O)[O:11]1)=[N+:7]=[N-:8].C(N(CC)CC)C.[N-:32]=[N+:33]=[N-:34].[Li+]>C(Cl)Cl.C(OCC)C.O>[N:6]([CH2:9][C@H:10]1[C:15]2[C:16]([CH3:22])=[CH:17][CH:18]=[C:19]([O:20][CH3:21])[C:14]=2[CH2:13][C@@H:12]([CH2:23][N:32]=[N+:33]=[N-:34])[O:11]1)=[N+:7]=[N-:8]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 88163Lithium azideHCID 86744625HCID 86744625, compound

Product 1

HCID 56997872HCID 56997872, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (0.128 mL, 1.65 mmol) is added dropwise to a solution of [1R,3S] 1-azidomethyl-3,4-dihydro-3-hydroxymethyl-5-methoxy-8-methyl-1H-2-benzopyran (395 mg, 1.5 mmol), from Step 4, and 0.314 mL (2.25 mmol) of triethylamine (TEA) in 15 mL of methylene chloride at 0° C. After stirring for 30 min at 0° C., the reaction mixture is transferred to a separatory funnel and diluted with diethyl ether. The layers are separated and the organic layer is washed with 2×20 mL of water, 2×15 mL of 1 N aqueous hydrochloric acid solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue is dissolved in 20 mL of DMF and 440 mg (9 mmol) of lithium azide is added. The reaction mixture is heated to 80° C. and stirred at 80° C. for 4 h then cooled and poured into 50 mL of water. The aqueous solution is extracted with 3×30 mL of diethyl ether and the combined ether extracts are washed with 30 mL of water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified on silica gel to give the title compound.

Workup

  1. customthe reaction mixture is transferred to a separatory funnel
  2. customThe layers are separated
  3. washthe organic layer is washed with 2×20 mL of water, 2×15 mL of 1 N aqueous hydrochloric acid solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue is dissolved in 20 mL of DMF
  8. temperatureThe reaction mixture is heated to 80° C.
  9. stirringstirred at 80° C. for 4 h
  10. temperaturethen cooled
  11. extractionThe aqueous solution is extracted with 3×30 mL of diethyl ether
  12. washthe combined ether extracts are washed with 30 mL of water and brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe residue is purified on silica gel

Sources & evidence

ORD record
ord-3bb7220c3b834e3694201b4fa424b9fe
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

Loading…