p-Toluenesulfonic acid → HCID 10252901, compound

HRID 561769Notes

Reaction equation

HRID 561769 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C@H:10]([OH:38])/[CH:11]=[CH:12]/[C@H:13]1[C@@H:17]([F:18])[CH2:16][C@H:15]([O:19]C2CCCCO2)[C@@H:14]1[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C.O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C@H:10]([OH:38])/[CH:11]=[CH:12]/[C@H:13]1[C@@H:17]([F:18])[CH2:16][C@H:15]([OH:19])[C@@H:14]1[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH:35]([CH3:36])[CH3:37])=[O:33]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 12073627HCID 12073627, compound

Product 1

HCID 10252901HCID 10252901, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a stirring mixture consisting of (Z)-isopropyl 7-((1R,2R,3S,5S)-2-((S,E)-3-(2,3-dihydro-1H-inden-2-yl)-3-hydroxyprop-1-enyl)-3-fluoro-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate (prepared in Step I, 15.2 g) in a 10:1 isopropanol-water solution (300 mL) was added p-toluenesulfonic acid (1 g) and the reaction mixture was heated to 50° C. The reaction progress was monitored by TLC. Upon completion of reaction, the reaction mixture was evaporated to dryness and redissolved in ethyl acetate. The organic solution was washed twice with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified on silica gel. Elution with hexanes-ethyl acetate (9:1) afforded the title intermediate (2.2 g).

Workup

  1. customUpon completion of reaction
  2. customthe reaction mixture was evaporated to dryness
  3. dissolutionredissolved in ethyl acetate
  4. washThe organic solution was washed twice with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified on silica gel
  9. washElution with hexanes-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-5cf5fa32d2a4415da3ea3c09b16e6141
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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