Water → HCID 22476614, compound

HRID 2184399Notes

Reaction equation

HRID 2184399 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:13][CH:11]([S:8]([NH:7][CH:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])(=[O:10])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 22476566(2-Hydroxycyclopentyl)[(methylethyl)sulfonyl]amine

Product 1

HCID 22476614HCID 22476614, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-55 °C

Procedure

Scheme IA, step C: Into a flame dried 500 mL 3 neck flask fitted with a thermometer and magnetic stirrer, DMSO (6.16 mL) in methylene chloride (20 mL) was added dropwise to oxalyl chloride (3.80 mL) in methylene chloride (100 mL) while stirring at −55° C. under a nitrogen atmosphere. After 2 minutes, (2-hydroxycyclopentyl)[(methylethyl)sulfonyl]amine (8.00 g, 38.6 mmol) in methylene chloride (45 mL) was added dropwise at this temperature and the reaction was stirred for an additional 15 minutes. Triethylamine (25.5 mL) was then added dropwise and the reaction was allowed to warm to room temperature. 180 mL of water was added at room temperature and the layers were separated. The organic layer was washed once with water, dried over potassium carbonate, filtered, and concentrated under reduced vacuum to yield 7.83 g as a dark oil. This material was purified via silica gel chromatography employing the Water's Prep. 2000 and eluting with a solvent of methylene chloride/ethyl acetate 9:1 to provide the intermediate title compound (5.76 g, 73%) as a yellow oil. Ion Spray M.S. 204.1 (M*−1). Calculated for C8H15NO3S: Theory: C, 46.81; H, 7.37; N, 6.82. Found: C, 46.56; H, 7.32; N, 6.77.

Workup

  1. dry with materialScheme IA, step C: Into a flame dried 500 mL 3 neck flask
  2. customfitted with a thermometer and magnetic stirrer, DMSO (6.16 mL) in methylene chloride (20 mL)
  3. additionwas added dropwise to oxalyl chloride (3.80 mL) in methylene chloride (100 mL)
  4. stirringthe reaction was stirred for an additional 15 minutes
  5. temperatureto warm to room temperature
  6. customthe layers were separated
  7. washThe organic layer was washed once with water
  8. dry with materialdried over potassium carbonate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced vacuum
  11. customto yield 7.83 g as a dark oil
  12. customThis material was purified via silica gel chromatography
  13. wash2000 and eluting with a solvent of methylene chloride/ethyl acetate 9:1

Sources & evidence

ORD record
ord-2128782b4dc24232aaf0216c86a3b52c
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

Loading…