Sodium Hydroxide → 2-[(1S,2R)-1,2-diphenyl-2-propoxyethyl]-1,2-thiazolidine 1,1-dioxide

HRID 1170394Notes

Reaction equation

HRID 1170394 reaction equation
[O:1]=[S:2]1(=[O:22])[CH2:6][CH2:5][CH2:4][N:3]1[C@@H:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9].[OH-].[Na+].[CH2:25](I)[CH2:26][CH3:27]>CS(C)=O.O>[C:16]1([C@H:7]([N:3]2[CH2:4][CH2:5][CH2:6][S:2]2(=[O:22])=[O:1])[C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:9][CH2:25][CH2:26][CH3:27])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 336431-IodopropaneHCID 67524037HCID 67524037, compound

Product 1

HCID 120033822-[(1S,2R)-1,2-diphenyl-2-propoxyethyl]-1,2-thiazolidine 1,1-dioxide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The product obtained from stage b) (70 mg, 0.221 mmol) was dissolved in 1 ml of DMSO, and 110 mg of powdered NaOH and then 169 mg (0.995 mmol) of n-propyl iodide were added. The reaction mixture was stirred at room temperature for 1.5 hours and then diluted with water. The crystalline precipitate obtained thereby was filtered off with suction. After drying, the material was stirred several times with n-heptane. 14.5 mg of (1S,2R)-2-(1,2-diphenyl-2-propoxyethyl)isothiazolidine 1,1-dioxide were obtained.

Workup

  1. customThe crystalline precipitate obtained
  2. filtrationthereby was filtered off with suction
  3. customAfter drying
  4. stirringthe material was stirred several times with n-heptane

Sources & evidence

ORD record
ord-79108b8bc8424ed5a5d8b3f0cfe985c0
Source dataset
uspto-grants-2010_11
Patent number
US07825264B2

Reaction notes

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