p-Toluenesulfonic acid monohydrate → HCID 10318924, compound

HRID 651799Notes

Reaction equation

HRID 651799 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:22]([NH:24][N:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(OCC)(=O)C>[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:22]([NH:24][N:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:10]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86757307HCID 86757307, compound

Product 1

HCID 10318924HCID 10318924, compoundYield 30.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.298 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-4-methyl-N-(2,4-dioxo-1-imidazolidinyl)valeramide in 3 ml of methanol was treated with 0.030 g of p-toluenesulphonic acid monohydrate. The mixture was stirred for 3.5 hours at room temperature and then 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. The residue was triturated with diethyl ether to give 0.076 g of (E)-2(R)-[1(S)-(Hydroxycarbamoyl)-4-phenyl-3-butenyl]-4-methyl-N-(2,4-dioxo-1-imidazolidinyl)valeramide 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. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-23923490a06b4ca1859a60a0d47506ed
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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