Water → HCID 15486877, compound

HRID 1373482Notes

Reaction equation

HRID 1373482 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 magnetic stirring. The reaction mixture is stirred at ambient 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 on silica gel (eluant:acetone/cyclohexane (2/8)).

Workup

  1. extractionfollowed by extraction with CH2Cl2
  2. washThe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe resulting oil is purified by chromatography on silica gel (eluant:acetone/cyclohexane (2/8))

Sources & evidence

ORD record
ord-740f205361f14166b7405d6722ea3acd
Source dataset
uspto-grants-2007_01
Patent number
US07161035B2

Reaction notes

Loading…