p-Toluenesulfonic acid → HCID 68907300, compound

HRID 546468Notes

Reaction equation

HRID 546468 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][C@@H:13]1[NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]1(C)C=CC(S(O)(=O)=O)=CC=1.[O:41]1CCC[CH2:42]1>CO.COC(OC)(C)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][C:15]([O:41][CH3:42])([O:18][CH3:30])[CH2:14][C@@H:13]1[NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 68905424HCID 68905424, compound

Product 1

HCID 68907300HCID 68907300, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

(±)-cis-N1,N2-Bis(benzyloxycarbonyl)-4-oxo-1,2-cyclohexanediamine (3.89 g) was dissolved in a mixed solvent of methanol (15 ml) and tetrahydrofuran (15 ml), 2,2-dimethoxypropane (10.7 ml) and p-toluenesulfonic acid (187 mg) were added, and the mixture was stirred at room temperature for 3 hours. The solvent was concentrated, and a saturated aqueous solution of sodium hydrogencarbonate was added to conduct extraction with ethyl acetate. After the resultant organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane 1:2) to obtain the title compound (3.54 g) as a colorless amorphous solid.

Workup

  1. additionwere added
  2. concentrationThe solvent was concentrated
  3. additiona saturated aqueous solution of sodium hydrogencarbonate was added
  4. extractionextraction with ethyl acetate
  5. washAfter the resultant organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane 1:2)

Sources & evidence

ORD record
ord-f32bf881588f4928b1d2c9f1d72259c5
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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