p-Toluenesulfonic acid monohydrate → HCID 86757326, compound

HRID 651818Notes

Reaction equation

HRID 651818 reaction equation
[C:1]([NH:9][CH2:10][C@@H:11]([C@@H:22]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:23]([NH:25][N:26]1[C:30](=[O:31])[C@H:29]([CH:32]([CH3:34])[CH3:33])[NH:28][C:27]1=[O:35])=[O:24])[C:12](=[O:21])[NH:13][O:14]C1CCCCO1)(=[O:8])[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:1]([NH:9][CH2:10][C@@H:11]([C@@H:22]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:23]([NH:25][N:26]1[C:30](=[O:31])[C@H:29]([CH:32]([CH3:33])[CH3:34])[NH:28][C:27]1=[O:35])=[O:24])[C:12](=[O:21])[NH:13][OH:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86757327HCID 86757327, compound

Product 1

HCID 86757326HCID 86757326, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.22 g of 2(R)-[2-benzamido-1(R)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]ethyl]-N-(4(S)-isopropyl-2,5-dioxo-1-imidazolidinyl)-4-methylvaleramide in 5 ml of methanol was treated with 0.022 g of p-toluenesulphonic acid monohydrate. The mixture was stirred for 2.5 hours and evaporated. The residue was dissolved in ethyl acetate and washed with 5% aqueous sodium hydrogen carbonate and then saturated aqueous sodium chloride. The organic fraction was dried over anhydrous magnesium sulphate and evaporated. The residue was triturated with diethyl ether to give 0.14 g of 2(R)-[2-benzamido-1(R)-(hydroxycarbamoyl)ethyl]-N-(4(S)-isopropyl-2,5-dioxo-1-imidazolidinyl)-4-methylvaleramide 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 materialThe organic fraction was dried over anhydrous magnesium sulphate
  5. customevaporated
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-0f1c8c9955724f66a3a85404e1941232
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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