Sulfuric Acid → HCID 67188798, compound

HRID 546246Notes

Reaction equation

HRID 546246 reaction equation
[CH:1]1([CH2:6][C@H:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([S:28][CH3:29])[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:31].C(Cl)Cl>O1CCOCC1.O>[CH:1]1([CH2:6][C@H:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([S:28][CH3:29])[CH:23]=2)[C:8]([OH:9])=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 67191222HCID 67191222, compound

Product 1

HCID 67188798HCID 67188798, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of (R)-3-cyclopentyl-N-((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2-(3-methylsulfanyl-phenyl)-propionamide (1.16 g, 2.82 mmol) in 1,4-dioxane (10 mL) was added 9 N aqueous sulfuric acid (10 mL) and the reaction was stirred at 110° C. for 18 h. The reaction was cooled to 25° C. and diluted with water (25 mL) and poured into methylene chloride (30 mL). The layers were separated and the aqueous layer was extracted with methylene chloride (2×30 mL). The combined methylene chloride layers were washed with water and saturated sodium chloride solution and then dried over magnesium sulfate. Filtration and concentration afforded the crude product which was purified by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) to yield (R)-3-cyclopentyl-2-(3-methylsulfanyl-phenyl)-propionic acid (712 mg, 96%) as a white solid.

Workup

  1. temperatureThe reaction was cooled to 25° C.
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with methylene chloride (2×30 mL)
  4. washThe combined methylene chloride layers were washed with water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and concentration
  7. customafforded the crude product which
  8. customwas purified by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3a9799da377a44aba33f01a9037faa6a
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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