Triethylamine → HCID 86666719, compound

HRID 2401355Notes

Reaction equation

HRID 2401355 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[C:17]([CH:22](O)[CH3:23])=[N:18][O:19][C:20]=2[CH3:21])=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.CS(Cl)(=O)=O.[N-:37]=[N+:38]=[N-:39].[Na+]>O.CCOC(C)=O.C(Cl)Cl>[N:37]([CH:22]([C:17]1[C:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:9])=[C:20]([CH3:21])[O:19][N:18]=1)[CH3:23])=[N+:38]=[N-:39]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 67813222HCID 67813222, compound

Product 1

HCID 86666719HCID 86666719, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottomed flask was added (4-chlorophenyl)(2-(3-(1-hydroxyethyl)-5-methylisoxazol-4-yl)phenyl)methanone (0.092 g, 0.269 mmol), CH2Cl2 (3.0 mL), and Et3N (0.075 mL, 0.538 mmol). The vial was cooled to 0° C. before addition of methanesulfonyl chloride (0.025 mL, 0.323 mmol) and the reaction stirred for 45 min at 0° C. before quenching with water. The layers were separated and the aqueous extracted with CH2Cl2. The combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was taken up in DMF (2 mL) and sodium azide (0.053 g, 0.808 mmol) was added. The reaction was stirred at room temperature overnight before being diluted with water and EtOAc. The layers were separated and the aqueous was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (2-(3-(1-azidoethyl)-5-methylisoxazol-4-yl)phenyl)(4-chlorophenyl)methanone (0.073 g, 0.199 mmol). LC/MS m/z 389 [M+Na]+.

Workup

  1. custombefore quenching with water
  2. customThe layers were separated
  3. extractionthe aqueous extracted with CH2Cl2
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. stirringThe reaction was stirred at room temperature overnight
  8. customThe layers were separated
  9. extractionthe aqueous was extracted with EtOAc
  10. washThe combined organics were washed with brine
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-d3100ad2574e4e5995c14daf7ee9def3
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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