Acetyl chloride → HCID 18696167, compound

HRID 1870295Notes

Reaction equation

HRID 1870295 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([OH:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=O)(C)(C)C.C(N(CC)CC)C.[C:29]([Cl:32])(=[O:31])[CH3:30]>O1CCCC1>[ClH:32].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([O:21][C:29](=[O:31])[CH3:30])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18696107HCID 18696107, compound

Product 1

HCID 18696167HCID 18696167, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 3-(2-(N-t-butoxycarbonylamino)ethoxy)-5-hydroxy-1,2-benzisoxazole (100 mg) in tetrahydrofuran (5 ml) was added triethylamine (44 mg) and acetyl chloride (34 mg) with stirring at 5° C., and the mixture was then stirred at the same temperature for 15 minutes. The reaction mixture was poured into ice water (40 ml), extracted with ethyl acetate (twice each with 40 ml) and the combined extracts were dried over anhydrous magnesium sulphate and filtered. The solvent was evaporate under reduced pressure and the residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent, to give the title compound (101 mg, 88%) as a colorless powder.

Workup

  1. stirringthe mixture was then stirred at the same temperature for 15 minutes
  2. extractionextracted with ethyl acetate (twice each with 40 ml) and the combined extracts
  3. dry with materialwere dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customThe solvent was evaporate under reduced pressure
  6. customthe residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent

Sources & evidence

ORD record
ord-58ae4017ef25475eb1273f64f315da63
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

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