Methanesulfonic Acid → HCID 19069714, compound

HRID 2258116Notes

Reaction equation

HRID 2258116 reaction equation
Cl.[SH:2][CH:3]1[CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.Cl[CH2:15][CH2:16][N:17]=[C:18]=[S:19].[CH3:20][S:21]([OH:24])(=[O:23])=[O:22]>O1CCCC1>[CH3:20][S:21]([OH:24])(=[O:23])=[O:22].[SH:2][CH:3]1[CH2:6][N:5]([C:18]2[S:19][CH2:15][CH2:16][N:17]=2)[CH2:4]1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 1386612-Chloroethyl IsothiocyanateHCID 184032413-Methylthio-azetidine hydrochloride

Product 1

HCID 19069714HCID 19069714, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 63.3 mg of 3-mercaptoazetidine hydrochloride (12) obtained in the above Example 10 dissolved in 1.0 ml of dried tetrahydrofuran, there was added 0.07 ml of triethylamine in the stream of nitrogen at a room temperature, and the resulting solution was stirred for 30 minutes. To this solution, there was added dropwise a solution of 70.3 mg of 2-chloroethylisothiocyanate dissolved in dried tetrahydrofuran, and the resulting solution was further stirred for one hour. After the reaction liquid was cooled to 0° C., 0.04 ml of methanesulfonic acid was added dropwise, and the resulting solution was stirred for 30 minutes, and, then, the solvent was evaporated in a vacuum. To the obtained residue, there was added 1.0 ml of dried methanol, and the resulting solution was subjected to heating and reflux for one hour, and, then, the solvent was evaporated in a vacuum. The obtained residue was separated and purified by thin-layer chromatography, and, thus, there was obtained 53.4 mg (yield: 39.2%) of 3-mercapto-1-(1,3-thiazolin-2-yl)azetidine methanesulfonate (13) in the form of colorless oily matter.

Workup

  1. stirringthe resulting solution was further stirred for one hour
  2. customAfter the reaction liquid
  3. stirringthe resulting solution was stirred for 30 minutes
  4. customthe solvent was evaporated in a vacuum
  5. additionTo the obtained residue, there was added 1.0 ml of dried methanol
  6. temperatureto heating
  7. temperaturereflux for one hour
  8. customthe solvent was evaporated in a vacuum
  9. customThe obtained residue was separated
  10. custompurified by thin-layer chromatography

Sources & evidence

ORD record
ord-48ad49667a6e411d81dfe914082b16b0
Source dataset
uspto-grants-1997_08
Patent number
US05659043

Reaction notes

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