Hydrochloric Acid → HCID 68543218, compound

HRID 2243482Notes

Reaction equation

HRID 2243482 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[C:10]([Cl:14])=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1OS(C(F)(F)F)(=O)=O)=O.CC(C)([O-])C.[Na+].[C:29]([O:33][CH3:34])(=[O:32])[CH2:30][SH:31].Cl.BrC[C:38]([O:40][CH2:41][CH3:42])=[O:39].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:34][O:33][C:29]([C:30]1[S:31][C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:8]=3[S:9][C:5]=2[C:3]=1[O:2][CH2:1][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:32]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 23676156Sodium t-butoxideHCID 86605573HCID 86605573, compound

Product 1

HCID 68543218HCID 68543218, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

Steps B-C: 7-chloro-3-trifluoromethanesulfonyloxy-benzo[b]thiophene-2-carboxylic acid methyl ester (104 mg, 0.28 mmol) in DMF (2 ml) was added to a mixture of sodium tert-butoxide (54 mg, 0.56 mmol) and methyl thioglycolate dissolved in DMF (1 ml). After 16 hr, water was added and the mixture was neutralized with 1N HCl. It was then extracted with EtOAc, dried over MgSO4, filtered, and the solvent was removed in vacuo. An inseparable mixture of hydrolized starting material/desired product with a 1:1.6 ratio resulted. This mixture was then treated with ethyl bromoacetate (120 μl, 1.1 mmol) in the presence of K2CO3 (90 mg, 0.65 mmol) at 60° C. After 24 hr, water was added and the mixture was extracted with EtOAc. Removal of solvent and purification by reverse phase HPLC yielded 19 mg (16% over 2 steps) of 7-chloro-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester. HRMS (ESI-, m/z) calcd for [M-H]1−, 340.93506, found, 340.9345.

Workup

  1. extractionIt was then extracted with EtOAc
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. additionAn inseparable mixture
  6. customresulted
  7. waitAfter 24 hr
  8. extractionthe mixture was extracted with EtOAc
  9. customRemoval of solvent and purification by reverse phase HPLC

Sources & evidence

ORD record
ord-c225f7bd011b436bbec5bf1d13f7f7f0
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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