Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 18347212, compound

HRID 2269583Notes

Reaction equation

HRID 2269583 reaction equation
C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.O[CH2:17][C:18]1[S:19][C:20]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:21]([C:27]2[CH:32]=[CH:31][C:30]([S:33][CH3:34])=[CH:29][CH:28]=2)[C:22]=1[CH2:23][C:24]([OH:26])=[O:25]>C(Cl)Cl>[CH3:34][S:33][C:30]1[CH:31]=[CH:32][C:27]([C:21]2[C:22]3[CH2:23][C:24](=[O:26])[O:25][CH2:17][C:18]=3[S:19][C:20]=2[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 18347205HCID 18347205, compound

Product 1

HCID 18347212HCID 18347212, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-10-camphorsulfonic acid (5 mg) was added to a solution of [2-hydroxymethyl-4-(4-methylsulfanylphenyl)-5-phenylthiophen-3-yl]acetic acid (100 mg) (Step 3) in CH2Cl2 (5 mL) and the resulting solution was stirred overnight. The solution was diluted with CH2Cl and washed with a saturated solution of NaHCO3, dried over MgSO4, filtered and the solvent was evaporated under vacuum. Purification by silica gel chromatography using 20% of EtOAc in hexane gave the title compound.

Workup

  1. additionThe solution was diluted with CH2Cl
  2. washwashed with a saturated solution of NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was evaporated under vacuum
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-7cae710b25324f2a8aff2534b3301c0a
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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