Ethanol → HCID 56991489, compound

HRID 352678Notes

Reaction equation

HRID 352678 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C@@H:15]([CH2:19][NH:20][C:21](=[O:39])[C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](=[O:38])[NH:31][C:32]3[NH:33][CH2:34][CH2:35][CH2:36][N:37]=3)=[CH:24][CH:23]=2)[C:16]([OH:18])=[O:17])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:40](O)[CH3:41]>S(=O)(=O)(O)O>[CH2:40]([O:17][C:16](=[O:18])[C@@H:15]([NH:14][S:11]([C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)(=[O:13])=[O:12])[CH2:19][NH:20][C:21](=[O:39])[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](=[O:38])[NH:31][C:32]2[NH:37][CH2:36][CH2:35][CH2:34][N:33]=2)=[CH:24][CH:23]=1)[CH3:41]

Participants

4

Reactant 2

HCID 702EthanolHCID 11570362HCID 11570362, compound

Product 1

HCID 56991489HCID 56991489, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

700 mg of (2S)-2-(4-tert-butyl-benzenesulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid was dissolved in 100 ml of ethanol and 15 drops of concentrated sulfuric acid was added. The reaction solution was boiled for 3.5 hours. The solvent was removed in vacuo, the residue was dissolved in dichloromethane and washed three times with saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted once with dichloromethane and the combined organic phase was washed twice with saturated aqueous sodium chloride solution. The organic phase was dried with sodium sulfate, filtered and the solvent was removed in vacuo. The residue was dissolved in 2N aqueous hydrochloric acid. The hydrochloric acid was removed in vacuo, the residue was dissolved in acetonitrile and added to water. This mixture was lyophilized. Yield 480 mg. MS (ES+): m/e=586.4 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed three times with saturated aqueous sodium bicarbonate solution
  4. extractionThe aqueous phase was extracted once with dichloromethane
  5. washthe combined organic phase was washed twice with saturated aqueous sodium chloride solution
  6. dry with materialThe organic phase was dried with sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. dissolutionThe residue was dissolved in 2N aqueous hydrochloric acid
  10. customThe hydrochloric acid was removed in vacuo
  11. dissolutionthe residue was dissolved in acetonitrile
  12. additionadded to water

Sources & evidence

ORD record
ord-df5b8ae48863414d93fc2d9f4e9fa2c4
Source dataset
uspto-grants-2004_06
Patent number
US06747148B2

Reaction notes

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