p-Toluenesulfonic acid monohydrate → HCID 86757314, compound

HRID 651808Notes

Reaction equation

HRID 651808 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:22]([NH:24][N:25]1[C:29](=[O:30])[CH2:28][N:27]([CH3:31])[C:26]1=[S:32])=[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>[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:22]([NH:24][N:25]1[C:29](=[O:30])[CH2:28][N:27]([CH3:31])[C:26]1=[S:32])=[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

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86757315HCID 86757315, compound

Product 1

HCID 86757314HCID 86757314, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.209 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-4-methyl-N-(3-methyl-5-oxo-2-thioxo-1-imidazolidinyl)valeramide in 5 ml of methanol was treated with 0.020 g of p-toluenesulphonic acid monohydrate. The mixture was stirred for 2.5 hours at room temperature and then evaporated. The residue was dissolved in ethyl acetate and washed with 5% aqueous sodium hydrogen carbonate. The organic layer was dried over anhydrous magnesium sulphate and evaporated. The residue was triturated with diethyl ether/hexane (2:1) to give 0.048 g of (E)-2(R)-[1(S)-(Hydroxycarbamoyl)-4-phenyl-3-butenyl]-4-methyl-N-(3-methyl-5-oxo-2-thioxo-1-imidazolidinyl)valeramide in the form of a yellow solid.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 5% aqueous sodium hydrogen carbonate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  5. customevaporated
  6. customThe residue was triturated with diethyl ether/hexane (2:1)

Sources & evidence

ORD record
ord-71045d98c73e440caf97e915c002036c
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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