Water → HCID 15486877, compound

HRID 429777Notes

Reaction equation

HRID 429777 reaction equation
C(N(CC)CC)C.[S:8](Cl)([CH3:11])(=[O:10])=[O:9].O.[OH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][CH:25]=[C:26]2[CH2:29][CH2:30][NH:31][C:32](=[O:34])[CH3:33])=[CH:21][CH:20]=1>ClCCl>[CH3:11][S:8]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]2[C:27](=[C:26]([CH2:29][CH2:30][NH:31][C:32](=[O:34])[CH3:33])[CH:25]=[CH:24][CH:23]=2)[CH:28]=1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15486876HCID 15486876, compound

Product 1

HCID 15486877HCID 15486877, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

In a 250 ml round-bottomed flask, the alcohol obtained in Step A is dissolved in 50 ml of dichloromethane, and 0.012 mol of triethylamine is added. The mixture is cooled in an ice/salt bath at −10° C., and then 0.012 mol of mesyl chloride is added dropwise with stirring with a magnetic stirrer. The reaction mixture is stirred at room temperature for 4 hours. 100 ml of water are then added, followed by extraction with CH2Cl2. The organic phase is washed with water, dried over MgSO4 and evaporated under reduced pressure. The resulting oil is purified by chromatography over silica gel (eluant: acetone/cyclohexane (2/8)).

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 4 hours
  2. extractionfollowed by extraction with CH2Cl2
  3. washThe organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe resulting oil is purified by chromatography over silica gel (eluant: acetone/cyclohexane (2/8))

Sources & evidence

ORD record
ord-bbffdaf9c90c4fbab70f3268df60741a
Source dataset
uspto-grants-2001_11
Patent number
US06319930B1

Reaction notes

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