Ammonia → HCID 18696220, compound

HRID 1739055Notes

Reaction equation

HRID 1739055 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[C:17]([C:22]([OH:24])=O)=[C:18]([F:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=O)(C)(C)C.C([Cl:32])(=O)OCC(C)C.C([N:35](CC)CC)C.N>O1CCCC1>[ClH:32].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[C:17]([C:22](=[O:24])[NH2:35])=[C:18]([F:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 15453959HCID 15453959, compound

Product 1

HCID 18696220HCID 18696220, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 3-(2-(N-t-butoxycarbonylamino)ethoxy)-4-carboxy-5-fluoro-1,2-benzisoxazole (0.31 g) in tetrahydrofuran (20 ml) was added isobutyl chlorocarbonate (0.14 g) and triethylamine (0.11 g) with stirring at 5° C., and the mixture was then stirred for 15 minutes. Ammonia-saturated tetrahydrofuran solution (saturated at room temperature, 5 ml) was added to the reaction mixture and stirred for 15 minutes. The reaction mixture was poured into ice water (40 ml), extracted with diethylether (twice each with 40 ml) and the combined extracts were dried over anhydrous magnesium sulphate and filtered. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (4/1) as an eluent, to give title compound (0.24 g, 78% yield) as a colorless powder.

Workup

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

Sources & evidence

ORD record
ord-b94e6708a3494bf1b072ab392eca0b7e
Source dataset
uspto-grants-1999_10
Patent number
US05965591

Reaction notes

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