4-Toluenesulfonyl chloride → HCID 131718418, compound

HRID 1034497Notes

Reaction equation

HRID 1034497 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%. NMR δ(CDCl3) ppm: 2.2 to 2.5(m), 2.44(s, 3H), 2.98(s, 3H), 3.4 to 3.6(m, 2H), 3.82(s, 3H), 3.8 to 4.6(m), 5.03, 4.95(ABq, J=12 Hz, 2H), 5.2 (br s, 1H), 6.89(d, J=8.6 Hz, 2H), 7.18 to 7.4(m, 4H), 7.6 to 7.8(m, 2H). IR ν (CHCl3) cm-1 : 1698, 1612.

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-1a50f877ce404b4da43d21e5d788f3fe
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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