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

HRID 39008Notes

Reaction equation

HRID 39008 reaction equation
[F: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]([F: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 66878306HCID 66878306, compound

Product 1

HCID 86652937[(2R)-5-fluoro-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 10 using [[(2S)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.97 g, 3.7 mmol), DCM (20 ml), p-toluenesulfonyl chloride (1.06 g, 5.6 mmol), TEA (0.78 ml, 5.6 mmol) and 4-DMAP (0.46 g, 3.7 mmol). Yield: 1.47 g. MS m/z (rel. intensity, 70 eV) 416 (M+, 40), 244 (bp), 243 (26), 231 (19), 91 (50).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-34253c481f544bc9a00407a9166f622c
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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