4-Toluenesulfonyl chloride → HCID 131718418, compound

HRID 1941591Notes

Reaction equation

HRID 1941591 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]2[CH2:21][OH:22])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>ClCCl.CN(C)C1C=CN=CC=1>[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([O:22][CH2:21][C@@H:12]2[CH2:13][C@@H:14]([O:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH2:15][N:11]2[C:9]([O:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:24][CH:23]=2)=[O:10])(=[O:40])=[O:39])=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 22851796HCID 22851796, compound

Product 1

HCID 131718418HCID 131718418, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (8.7 g: 24.2 mmole) in dichloromethane(80 ml) are added triethylamine (4.05 ml), p-toluenesulfonyl chloride (5.08 g) and 4-dimethylaminopyridine (148 mg). The mixture is stirred at room temperature overnight. The reaction mixture is washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene: ethyl acetate=1:1) to give (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol p-toluenesulfonate (11.75 g). Yield: 95%.

Workup

  1. washThe reaction mixture is washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel column chromatography (toluene: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-815276511cc047f2ac3513ea6a10cf8e
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

Loading…