3-Methoxypropyne → HCID 23047376, compound

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

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).