Water → HCID 22476611, compound

HRID 2184411Notes

Reaction equation

HRID 2184411 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:14][CH:12]([S:9]([NH:8][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]1=[O:1])(=[O:11])=[O:10])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 22476602HCID 22476602, compound

Product 1

HCID 22476611HCID 22476611, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-55 °C

Procedure

Into a flame dried 250 mL 3 neck flask fitted with a thermometer and magnetic stirrer, DMSO (2.61 mL) in methylene chloride (10 mL) was added dropwise to oxalyl chloride (1.60 mL) in methylene chloride (50 mL) while stirring at −55° C. under a nitrogen atmosphere. After 2 minutes, (2-hydroxycyclohexyl)[(methylethyl)sulfonyl]amine (3.60 g, 16.3 mmol) in methylene chloride (10 mL) was added dropwise at this temperature and the reaction was stirred for an additional 15 minutes. Triethylamine (10.8 mL) was then added dropwise and the reaction was allowed to warm to room temperature. Water (76 mL) 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 3.90 g as an orange solid. This material was purified via silica gel chromatography employing the Water's Prep. 2000 and eluting with a solvent of methylene chloride/ethyl acetate 19:1 to yield the intermediate title compound (2.94 g, 82%) as a white solid. FD M.S. 219.2 (M*). Calculated for C9H17NO3S: Theory: C 49.29, H 7.81, N 6.39. Found: C 49.18, H 7.84, N 6.39.

Workup

  1. dry with materialInto a flame dried 250 mL 3 neck flask
  2. customfitted with a thermometer and magnetic stirrer, DMSO (2.61 mL) in methylene chloride (10 mL)
  3. additionwas added dropwise to oxalyl chloride (1.60 mL) in methylene chloride (50 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 3.90 g as an orange solid
  12. customThis material was purified via silica gel chromatography
  13. wash2000 and eluting with a solvent of methylene chloride/ethyl acetate 19:1

Sources & evidence

ORD record
ord-07b6a65c230243c9b18cb0263f3e9712
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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