p-Toluenesulfonic acid → HCID 57556922, compound

HRID 503207Notes

Reaction equation

HRID 503207 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][OH:19])[CH:13]=2)=[C:7]([NH2:20])[CH:6]=1)[CH3:2].[CH2:22](OC(OCC)OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][OH:19])[CH:13]=3)[CH:22]=[N:20][C:7]=2[CH:6]=1)=[O:21])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 57556921HCID 57556921, compound

Product 1

HCID 57556922HCID 57556922, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 6 (8.5 g), triethylorthoformate (7.55 mL), p-toluene sulphonic acid (2 g) in THF (75 mL) was stirred at reflux for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (600 mL), washed with 20% NaHCO3 solution and brine, successively, and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel using a 4:6 mixture of ethyl acetate and pet-ether as the eluent to afford compound 7 (7.9 g, 77%) as a solid.

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2 (600 mL)
  4. washwashed with 20% NaHCO3 solution and brine
  5. dry with materialsuccessively, and dried over anhydrous Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe crude product was purified by column chromatography on silica gel using
  8. additiona 4:6 mixture of ethyl acetate and pet-ether as the eluent

Sources & evidence

ORD record
ord-f6259f380f854fd4bee8ddc7e4d28e6d
Source dataset
uspto-grants-2010_08
Patent number
US07776900B2

Reaction notes

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