Methanesulfonic Acid → HCID 67316404, compound

HRID 1013820

Reaction equation

HRID 1013820 reaction equation
C([O:8][C:9]1[CH:30]=[C:29]([Cl:31])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([CH:19]3[C:27]4[NH:26][N:25]=[CH:24][C:23]=4[CH2:22][CH2:21][CH2:20]3)[C:15]2=[O:28])=[C:11]([Cl:32])[CH:10]=1)C1C=CC=CC=1.CS(O)(=O)=O>CSC>[Cl:31][C:29]1[CH:30]=[C:9]([OH:8])[CH:10]=[C:11]([Cl:32])[C:12]=1[CH2:13][C@@H:14]1[CH2:18][CH2:17][N:16]([CH:19]2[C:27]3[NH:26][N:25]=[CH:24][C:23]=3[CH2:22][CH2:21][CH2:20]2)[C:15]1=[O:28]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 67316393(R)-3-(4-benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-7-yl)-pyrrolidin-2-one

Product 1

HCID 67316404HCID 67316404, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 1068Dimethyl SulfideSolvent

Procedure

To a solution of (R)-3-(4-benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-7-yl)-pyrrolidin-2-one (2.46 g, 5.23 mmol) in dimethylsulfide (28 mL), add methane sulfonic acid (8.23 g, 85.7 mmol) and stir the mixture vigorously under at room temperature for 18 hours. Remove the solvent in vacuo and dilute the residue with water, adjust the pH to pH=7 with 5 N NaOH, and extract the mixture several times with ethyl acetate and THF. After drying the combined organic layer (Na2SO4), filter and concentrate under vacuum to afford 2.20 g (100%) of the title compound. MS (m/z): 381 (M+).

Workup

  1. customRemove the solvent in vacuo
  2. additiondilute the residue with water
  3. extractionextract the mixture several times with ethyl acetate and THF
  4. dry with materialAfter drying the combined organic layer (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-18d1d8da0f5f4e8d83285295930e5853
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Linked notes

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