4-Chlorobenzenesulfonyl chloride → HCID 10039936, compound

HRID 1375195Notes

Reaction equation

HRID 1375195 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C@H:13]([CH2:18][OH:19])[C@H:14]([CH2:16][CH3:17])[CH3:15].CCN(CC)CC>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C@H:13]([CH2:18][OH:19])[C@H:14]([CH2:16][CH3:17])[CH3:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 272402724629-25-2

Product 1

HCID 10039936HCID 10039936, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-chlorobenzenesulfonyl chloride (1.93 g, 9.1 mmol) in CH3CN (25 mL) and (S)-isoleucinol (1.07 g, 9.1 mmol) was added Et3N (1.91 mL, 13.7 mmol). The reaction mixture was stirred at 25° C. for 30 minutes. The solvent was removed and the oil was dissolved in CH2Cl2 (20 mL). The solution was washed with water (2×20 mL) and dried over Na2SO4. The solvent was removed to give N-4-chloro benzenesulfonyl isoleucinol, which was carried on without further purification.

Workup

  1. customThe solvent was removed
  2. dissolutionthe oil was dissolved in CH2Cl2 (20 mL)
  3. washThe solution was washed with water (2×20 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-33bc4dfd838546f3817b6da26b1409b6
Source dataset
uspto-grants-2007_01
Patent number
US07166622B2

Reaction notes

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