4-Toluenesulfonyl chloride → HCID 87281347, compound

HRID 1890434Notes

Reaction equation

HRID 1890434 reaction equation
[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][CH2:7][CH2:8][C@H:9]([OH:12])[CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16].C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([Si:5]([CH3:13])([CH3:14])[O:6][CH2:7][CH2:8][C@H:9]([OH:12])[CH2:10][O:11][S:15]([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 87315012HCID 87315012, compound

Product 1

HCID 87281347HCID 87281347, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2S)-4-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol (23.9 g, 108 mmol; second eluting compound in Preparation C, step C.i) and DMAP (2.65 g, 0.2 eq) in DCM (80 mL) cooled to 0° C. were added TEA (43.8 mL, 2.9 eq.) and a solution of TsCl (20.7 g, 1.1 eq.) in DCM (15 mL). The mixture was stirred at rt for 5 h, poured on sat. aq. NaHCO3 and extracted with DCM. The org. layer was dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 2:1) to afford the title intermediate as a colourless oil (31.3 g, 77% yield).

Workup

  1. extractionextracted with DCM
  2. dry with materiallayer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by CC (Hept/EA 2:1)

Sources & evidence

ORD record
ord-f6ec36c7eb3f4544853aab0c49954b7b
Source dataset
uspto-grants-2013_08
Patent number
US08507478B2

Reaction notes

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