p-Toluenesulfonic acid → HCID 25221316, compound

HRID 1024390Notes

Reaction equation

HRID 1024390 reaction equation
[CH2:1]([N:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3([CH2:23][O:24]C4CCCCO4)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[C:7]([Cl:31])[C:6]1=[O:32])[CH2:2][CH2:3][CH3:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([N:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3([CH2:23][OH:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[C:7]([Cl:31])[C:6]1=[O:32])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 25221315HCID 25221315, compound

Product 1

HCID 25221316HCID 25221316, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of compound E2 (0.10 g, 0.22 mmol) and a catalytic amount of p-toluenesulfonic acid in methanol (10 ml) was stirred at room temperature for 1 hour. The solvent was evaporated in vacuo and the resulting residue was taken up with DCM, washed with an aqueous saturated solution of NaHCO3, the combined organic extracts were dried (Na2SO4) and the solvent was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; 0-30% EtOAc/DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield E3 (0.05 g, 61%) as a colourless oil. Compounds E4 to E9 (Table 1) were prepared in a similar manner. Physico-Chemical Data LCMS—General Procedure

Workup

  1. customThe solvent was evaporated in vacuo
  2. washwashed with an aqueous saturated solution of NaHCO3
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. customthe solvent was evaporated in vacuo
  5. customThe crude residue was purified by column chromatography (silica gel; 0-30% EtOAc/DCM as eluent)
  6. customThe desired fractions were collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-33c8d2730f244159aaac37efe8918750
Source dataset
uspto-grants-2014_05
Patent number
US08722894B2

Reaction notes

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