Sulfuric Acid → HCID 67188777, compound

HRID 546267Notes

Reaction equation

HRID 546267 reaction equation
[CH:1]1([CH2:6][C@H:7]([C:22]2[CH:27]=[CH:26][C:25]([S:28][CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[C:24]([Cl:34])[CH:23]=2)[C:8](N([C@H](C)[C@H](O)C2C=CC=CC=2)C)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)[OH:36]>O1CCOCC1.O>[Cl:34][C:24]1[CH:23]=[C:22]([C@@H:7]([CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]([OH:9])=[O:36])[CH:27]=[CH:26][C:25]=1[S:28][CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 67190721HCID 67190721, compound

Product 1

HCID 67188777HCID 67188777, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A solution of (R)-3-cyclopentyl-2-(3-chloro-4-cyclopentylsulfanyl-phenyl)-N-((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-propionamide (1.5 mmol) in dioxane (5 mL) is treated with a 9 N aqueous sulfuric acid solution (1.5 mL). The resulting solution is then heated at 105° C. for 16 h. The reaction is then cooled and diluted with water (13 mL) and extracted with a chloroform/methanol solution (3:2, 3×20 mL) and then combined the organic extracts and dried over magnesium sulfate, filtered and concentrated. Purification on an AnaLogix Intelliflash system (silica gel column) will afford (R)-2-(3-chloro-4-cyclopentylsulfanyl-phenyl)-3-cyclopentyl-propionic acid.

Workup

  1. temperatureThe reaction is then cooled
  2. extractionextracted with a chloroform/methanol solution (3:2, 3×20 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on an AnaLogix Intelliflash system (silica gel column)

Sources & evidence

ORD record
ord-2ec58e10466e41758c62e62530bfd887
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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