Triphenylphosphine → 1-(4,5-Dihydro-1,3-thiazol-2-yl)azetidine-3-thiol--hydrogen chloride (1/1)
Reaction equation
[ClH:1].[SH:2][CH:3]1[CH2:6][NH:5][CH2:4]1.CS[C:9]1[S:10][CH2:11][CH2:12][N:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[ClH:1].[SH:2][CH:3]1[CH2:6][N:5]([C:9]2[S:10][CH2:11][CH2:12][N:13]=2)[CH2:4]1Participants
Procedure
To a solution of 22.7 mg of 3-mercaptoazetidine hydrochloride (12) obtained in the above Example 11 dissolved in 95% methanol (including 1 ml of water), there were added 26.6 mg of 2-(methylthio)-1,3-thiazoline and 5.2 mg of triphenylphosphine, and the resulting solution was subjected to heating and reflux for six hours. After the reaction was over, the solvent was evaporated in a vacuum, and the obtained residue was dissolved in a 0.1N hydrochloric acid, and the resulting mixture was washed with ethylacetate. The solvent in the obtained aqueous layer was evaporated in a vacuum, and the obtained residue was separated and purified by high performance liquid chromatography, and, thus, there was produced 29.1 mg (yield: 73.4%) of 3-mercapto-1-(1,3-thiazolin-2-yl)azetidine hydrochloride (8) in the form of colorless needle crystal.
Workup
- temperatureto heating
- temperaturereflux for six hours
- customwas evaporated in a vacuum
- dissolutionthe obtained residue was dissolved in a 0.1N hydrochloric acid
- washthe resulting mixture was washed with ethylacetate
- customThe solvent in the obtained aqueous layer was evaporated in a vacuum
- customthe obtained residue was separated
- custompurified by high performance liquid chromatography
Sources & evidence
- ORD record
- ord-9595be85c13249c3aa2010aea023330f
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05659043
Reaction notes
Loading…