4-Toluenesulfonyl chloride → [(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

HRID 39028Notes

Reaction equation

HRID 39028 reaction equation
[Cl:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([CH2:12][OH:13])[O:7][C:6]=2[CH:5]=[C:4]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:28][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:13][CH2:12][C@@H:8]2[O:7][C:6]3[CH:5]=[C:4]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=[C:2]([Cl:1])[C:11]=3[O:10][CH2:9]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 67199583HCID 67199583, compound

Product 1

HCID 86652939[(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Preparation according to Preparation 22 using [(2S)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.33 g, 1.2 mmol), DCM (10 ml), p-toluenesulfonyl chloride (0.34 g, 1.8 mmol), TEA (0.18 ml, 1.8 mmol) and 4-DMAP (0.15 g, 1.2 mmol). Yield: 0.47 g. MS m/z (rel. intensity, 70 eV) 344 (28), 342 (bp), 340 (74), 263 (18), 233 (31). Molecular ion not found, however fragmentation consistent with the title compound. Used directly in the next step (Example 38) without further analysis.

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-0d5cc5fa384945f4925311446cb5d14a
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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