4-Toluenesulfonyl chloride → HCID 178500380, compound

HRID 252392Notes

Reaction equation

HRID 252392 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]([C@H:7]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]1)([CH3:6])[CH3:5].C(N(CC)CC)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3](=[O:14])[C:4]([CH3:6])([C@H:7]1[CH2:8][CH2:9][C@H:10]([O:13][S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[CH2:11][CH2:12]1)[CH3:5]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178500377HCID 178500377, compound

Product 1

HCID 178500380HCID 178500380, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.400 g trans-2-(4-hydroxy-cyclohexyl)-2-methyl-propionic acid methyl ester (residue HH) are dissolved in 10 ml of dichloromethane. Triethylamine (0.42 ml) and 4-dimethylamino pyridine (0.012 g) are added and the solution is cooled to 0° C. 0.419 g of para-toluenesulfonyl chloride are added portionwise and the reaction mixture is then stirred at room temperature for 16 hours. The reaction mixture is poured onto saturated aqueous sodium hydrogencarbonate solution and the layers are separated. The aqueous layer is extracted with dichloromethane and the combined organics are dried over sodium sulphate and concentrated. Flash chromatography (SiO2 60F) of the residue provides the title compound which is identified on the basis of its Rf-value.

Workup

  1. customthe layers are separated
  2. extractionThe aqueous layer is extracted with dichloromethane
  3. dry with materialthe combined organics are dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-791e21fff0354eeab8dfb5a829bac964
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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