3-Methoxypropyne → HCID 23047376, compound

HRID 2107059Notes

Reaction equation

HRID 2107059 reaction equation
Cl[O-].[Na+].Cl.[CH2:5]([O:12][C:13]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:14]=1[C:15]1[C:16]([CH2:39][O:40][CH3:41])=[C:17]([CH:36]=[N:37][OH:38])[N:18]=[CH:19][C:20]=1[N:21]2S(C1C=CC(C)=CC=1)(=O)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:42][O:43][CH2:44][C:45]#[CH:46]>O1CCCC1>[CH2:5]([O:12][C:13]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:14]=1[C:15]1[C:16]([CH2:39][O:40][CH3:41])=[C:17]([C:36]3[CH:46]=[C:45]([CH2:44][O:43][CH3:42])[O:38][N:37]=3)[N:18]=[CH:19][C:20]=1[NH:21]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 693933-MethoxypropyneHCID 23665760Sodium HypochloriteHCID 136364615HCID 136364615, compound

Product 1

HCID 23047376HCID 23047376, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At room temperature under a protective gas, 1.4 ml of sodium hypochlorite solution is added dropwise to 155 mg of 5-benzyloxy-4-methoxymethyl-9-tosyl-β-carboline-3-carbaldehyde oxime hydrochloride in 6 ml of absolute tetrahydrofuran. The mixture is stirred until the oxime has disappeared (TLC control) for one hour at room temperature, then 210 mg of methylpropargyl ether is added dropwise and the mixture is agitated overnight at room temperature. After the solvent has been removed by distillation, the mixture is distributed in ethyl acetate/water, and the organic phase is dried over magnesium sulfate, filtered, and concentrated. The residue is dissolved in 8 ml of methanol, combined with 54 mg of sodium methylate, and heated to reflux for one hour. After concentration and distribution in ethyl acetate/concentrated sodium chloride solution, the organic phase is dried, filtered, and concentrated. The residue is chromatographed over silica gel with toluene+ethyl acetate in a ratio of 1:1. The corresponding fractions are combined and crystallized from ethyl acetate, thus obtaining 70 mg, melting point 133°-135° C. (ethyl acetate).

Workup

  1. customfor one hour
  2. customat room temperature
  3. customAfter the solvent has been removed by distillation
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue is dissolved in 8 ml of methanol
  8. temperatureheated
  9. temperatureto reflux for one hour
  10. concentrationAfter concentration and distribution in ethyl acetate/concentrated sodium chloride solution
  11. customthe organic phase is dried
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe residue is chromatographed over silica gel with toluene+ethyl acetate in a ratio of 1:1
  15. customcrystallized from ethyl acetate
  16. customthus obtaining 70 mg, melting point 133°-135° C. (ethyl acetate)

Sources & evidence

ORD record
ord-44892a9be4c44d6e9d28182287d3585c
Source dataset
uspto-grants-1990_06
Patent number
US04933345

Reaction notes

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