Methyl propiolate → HCID 18783759, compound

HRID 1108551Notes

Reaction equation

HRID 1108551 reaction equation
[C:1]([NH:4][CH:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]=[N+:17]=[N-:18])=[C:12]([F:19])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].[C:20]([O:24][CH3:25])(=[O:23])[C:21]#[CH:22]>C1C=CC=CC=1>[C:1]([NH:4][CH:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH:22]=[C:21]([C:20]([O:24][CH3:25])=[O:23])[N:18]=[N:17]3)=[C:12]([F:19])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 13536Methyl propiolateHCID 18783761HCID 18783761, compound

Product 1

HCID 18783759HCID 18783759, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
105 °C

Procedure

5-Acetamido-3-(4-azido-3-fluorophenyl)isoxazoline (277 mg) is combined with methyl propiolate (0.356 ml) in 3 ml benzene in a screw cap pressure tube under nitrogen. The reaction is warmed to 105° C. for 1 hour, is cooled to room temperature, and is washed into a recovery flask with ethyl acetate. The volatiles are removed in vucuo. The crude material is recrystallized from ethyl acetate to provide 252 mg (70%/) of 5-acetamido-3-(4-(4-carbomethoxy-1,2,3-triazol-1-yl)-3-fluorophenyl)isoxazoline as an off-white solid, mp 221° C.

Workup

  1. customcap pressure tube under nitrogen
  2. temperatureis cooled to room temperature
  3. washis washed into a recovery flask with ethyl acetate
  4. customThe volatiles are removed in vucuo
  5. customThe crude material is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a59d57e798184e76993d19036c659295
Source dataset
uspto-grants-2000_05
Patent number
US06069141

Reaction notes

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