p-Toluenesulfonic acid monohydrate → HCID 86757335, compound

HRID 651828Notes

Reaction equation

HRID 651828 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[O:14])[N:10]([NH:15][C:16](=[O:42])[C@@H:17]([C@@H:22]([C:32](=[O:41])[NH:33][O:34]C2CCCCO2)[CH2:23]/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]1=[O:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(OCC)(=O)C>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[O:14])[N:10]([NH:15][C:16](=[O:42])[C@@H:17]([C@@H:22]([C:32](=[O:41])[NH:33][OH:34])[CH2:23]/[CH:24]=[CH:25]/[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]1=[O:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86757336HCID 86757336, compound

Product 1

HCID 86757335HCID 86757335, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.045 g of (E)-N-(3-benzyl-2,4,5-trioxo-1-imidazolidinyl]-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-4-methylvaleramide in 2 ml of methanol was treated with 0.010 g of p-toluenesulphonic acid monohydrate and stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate and washed in sequence with 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulphate and evaporated to give a residue which was triturated with diethyl ether to give 0.032 g of (E)-N-(3-benzyl-2,4,5-trioxo-1-imidazolidinyl]-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-4-methylvaleramide in the form of a white solid.

Workup

  1. washwashed in sequence with 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  3. customevaporated
  4. customto give a residue which
  5. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-3685928975264a56921c3258d02f7338
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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