Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Methyl 5-(3-((1R,2R,3R,5R)-5-chloro-2-((3S,7R,E)-3,7-dihydroxyoct-1-enyl)-3-hydroxycyclopentyl)propyl)thiophene-2-carboxylate

HRID 1694332Notes

Reaction equation

HRID 1694332 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Si]([O:25][C@@H:26]([CH3:59])[CH2:27][CH2:28][CH2:29][C@H:30]([OH:58])/[CH:31]=[CH:32]/[C@H:33]1[C@H:37]([O:38]C2CCCCO2)[CH2:36][C@@H:35]([Cl:45])[C@@H:34]1[CH2:46][CH2:47][CH2:48][C:49]1[S:53][C:52]([C:54]([O:56][CH3:57])=[O:55])=[CH:51][CH:50]=1)(C(C)(C)C)(C)C>CO>[Cl:45][C@H:35]1[C@H:34]([CH2:46][CH2:47][CH2:48][C:49]2[S:53][C:52]([C:54]([O:56][CH3:57])=[O:55])=[CH:51][CH:50]=2)[C@@H:33](/[CH:32]=[CH:31]/[C@@H:30]([OH:58])[CH2:29][CH2:28][CH2:27][C@H:26]([OH:25])[CH3:59])[C@H:37]([OH:38])[CH2:36]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57734122Methyl 5-(3-((1R,2R,3R,5R)-2-((3S,7S,E)-7-(tert-butyldimethylsilyloxy)-3-hydroxyoct-1-enyl)-5-chloro-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)propyl)thiophene-2-carboxylate

Product 1

HCID 57734135Methyl 5-(3-((1R,2R,3R,5R)-5-chloro-2-((3S,7R,E)-3,7-dihydroxyoct-1-enyl)-3-hydroxycyclopentyl)propyl)thiophene-2-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridinium p-toluenesulfonate (20.4 mg, 0.081 mmol) was added to a solution of the THP-ether 15 (52 mg, 0.081 mmol) in MeOH (3 mL) at 23° C. The reaction was stirred for 24 h and then concentrated in vacuo. The residue was diluted with EtOAc and washed with 1N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product was purified by FCC (silica gel, 19:1 EtOAc/MeOH) to afford 34.9 mg (97%) of triol 11.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with 1N HCl, saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic portion was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by FCC (silica gel, 19:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-18341ed5a2894d85b94739f258d288ac
Source dataset
uspto-grants-2012_04
Patent number
US08158676B2

Reaction notes

Loading…