4-Toluenesulfonyl chloride → HCID 58513729, compound

HRID 2362727Notes

Reaction equation

HRID 2362727 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1.C(N(CC)CC)C.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>ClCCl.CN(C)C1C=CN=CC=1>[S:18]1[CH:19]=[CH:20][N:21]=[C:17]1[C:5]1([O:4][CH2:3][CH2:2][O:1][S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:11])[CH2:6]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 58513754HCID 58513754, compound

Product 1

HCID 58513729HCID 58513729, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ambient solution of tert-butyl 3-(2-hydroxyethoxy)-3-(thiazol-2-yl)pyrrolidine-1-carboxylate (1.92 g, 6.11 mmol) in dichloromethane (20 mL) was added triethylamine (1.70 mL, 12.21 mmol), 4-dimethylaminopyridine (0.075 g, 0.611 mmol), and para-toluenesulfonyl chloride (1.28 g, 6.72 mmol). The reaction was stirred for 16 hours and was quenched by the addition of saturated ammonium chloride solution. The layers were separated, and the aqueous layer was extracted with additional dichloromethane. The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the product, which was used without further purification. MS ESI(+) m/z 468.8 [M+H]+.

Workup

  1. customwas quenched by the addition of saturated ammonium chloride solution
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with additional dichloromethane
  4. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the product, which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-42656490fee74f18a21080252eff6790
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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