4-Toluenesulfonyl chloride → HCID 86625864, compound

HRID 1692189Notes

Reaction equation

HRID 1692189 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([O:19][CH2:20][C@@H:21]([CH2:32][OH:33])[O:22][CH2:23][P:24]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])=[O:25])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:33][CH2:32][C@@H:21]([O:22][CH2:23][P:24]([CH:26]([CH3:28])[CH3:27])([CH:29]([CH3:30])[CH3:31])=[O:25])[CH2:20][O:19][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 57445220HCID 57445220, compound

Product 1

HCID 86625864HCID 86625864, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

p-Tolylsulfonyl chloride (38.8 g, 204 mmol) was added to a solution of compound 6 (31 g) in dry pyridine (200 mL) cooled to 0° C. After 1 h stirring at 0° C. the mixture was stirred at room temperature (rt) for additional 24 h and evaporated in vacuo. The syrupy residue was chromatographed on a column of silica gel (1000 mL) in system toluene-ethyl acetate (5:1). After removal of rests of p-tolylsulfonyl chloride (RF 0.9) the compound 7 was eluted with system toluene-ethyl acetate (1:2), (RF 0.5). Product containing fractions were evaporated to give 18.7 g (77%) of 7 as a colorless syrup.

Workup

  1. stirringwas stirred at room temperature (rt) for additional 24 h
  2. customevaporated in vacuo
  3. customThe syrupy residue was chromatographed on a column of silica gel (1000 mL) in system toluene-ethyl acetate (5:1)
  4. customAfter removal
  5. washwas eluted with system toluene-ethyl acetate (1:2), (RF 0.5)
  6. additionProduct containing fractions
  7. customwere evaporated

Sources & evidence

ORD record
ord-356d06c9b848480083e75c1a2f46fd1e
Source dataset
uspto-grants-2012_04
Patent number
US08153787B2

Reaction notes

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