Hydroxylamine → HCID 45072299, compound

HRID 1023825Notes

Reaction equation

HRID 1023825 reaction equation
NO.CC[N:5]([CH2:8][CH3:9])[CH2:6]C.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.CS(Cl)(=O)=O.[Na+].[Cl-]>C(Cl)Cl.O>[CH3:11][C:10]([C@:8]1([CH3:9])[CH2:6][N:5]1[S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17])([CH3:20])[CH3:15]

Participants

8

Reactant 5

HCID 787HydroxylamineHCID 5234Sodium ChlorideHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride

Product 1

HCID 45072299HCID 45072299, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of the amino alcohol from Step 2 (4.98 g, 38.0 mmol) in CH2Cl2 (200 mL) at 0° C. was treated with Et3N (26 mL, 190 mmol) followed by a solution of p-toluenesulfonyl chloride (8.7 g, 45.6 mmol) in CH2Cl2 (50 mL) over 40 min. The reaction mixture was stirred at room temperature for 4 d. The mixture was cooled to 0° C. after which Et3N (8.50 mL, 60.8 mmol) and methanesulfonyl chloride (5.88 mL, 76.0 mmol) were added. The mixture was stirred at 0° C. for 4 h. The reaction mixture was poured into a 1:1 mixture of saturated aqueous NaCl and water and was extracted with CH2Cl2. The organic layer was washed with saturated aqueous NaCl, dried (Na2SO4) filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography, elution with 0-50% EtOAc in heptane, to provide the title compound (5.88 g, 58%) as a white solid.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at 0° C. for 4 h
  3. extractionwas extracted with CH2Cl2
  4. washThe organic layer was washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography, elution with 0-50% EtOAc in heptane

Sources & evidence

ORD record
ord-e3293975805c4e56995c716b28fdd52d
Source dataset
uspto-grants-2014_05
Patent number
US08722727B2

Reaction notes

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