p-Toluenesulfonic acid monohydrate → HCID 11452605, compound

HRID 651782Notes

Reaction equation

HRID 651782 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C@@H:21]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:22]([NH:24][N:25]2[C:29](=[O:30])[CH2:28][NH:27][C:26]2=[O:31])=[O:23])[C:11](=[O:20])[NH:12][O:13]C2CCCCO2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C@@H:21]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:22]([NH:24][N:25]2[C:29](=[O:30])[CH2:28][NH:27][C:26]2=[O:31])=[O:23])[C:11](=[O:20])[NH:12][OH:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11167840HCID 11167840, compound

Product 1

HCID 11452605HCID 11452605, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.280 g of 2(R)-[4-cyclohexyl-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]butyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide in 10 ml of methanol was treated with 0.028 g of p-toluenesulphonic acid monohydrate. The mixture was stirred for 2 hours at room temperature and evaporated. The residue was dissolved in ethyl acetate, washed with 5% aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulphate and evaporated. The residue was purified by flash column chromatography on silica gel using methanol/dichloromethane (1:9) for the elution to give 0.069 g of 2(R)-[4-cyclohexyl-1(S)-(hydroxycarbamoyl)butyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide in the form of a white solid.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 5% aqueous sodium hydrogen carbonate
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-5c71463e7a5c463da7564c19f9439112
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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