Hydrochloric Acid → HCID 178482828, compound

HRID 2351013Notes

Reaction equation

HRID 2351013 reaction equation
[CH3:1][S:2]([NH:5][C:6](=[N:14][CH2:15][CH2:16][S:17][CH2:18][C:19]1[O:20][C:21]([CH2:24][N:25]([CH3:32])[C:26](=[O:31])[C:27]([Cl:30])([Cl:29])[Cl:28])=[CH:22][CH:23]=1)OC1C=CC=CC=1)(=[O:4])=[O:3].[CH:33]1[C:38]([C@@H:39]([OH:42])[CH2:40][NH2:41])=[CH:37][CH:36]=[C:35]([OH:43])[CH:34]=1.C([O-])(=O)C.[K+].Cl>O.C(OCC)(=O)C.C(N(CC)CC)C.C(#N)C>[OH:42][CH:39]([C:38]1[CH:37]=[CH:36][C:35]([OH:43])=[CH:34][CH:33]=1)[CH2:40][NH:41][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[N:14][CH2:15][CH2:16][S:17][CH2:18][C:19]1[O:20][C:21]([CH2:24][N:25]([CH3:32])[C:26](=[O:31])[C:27]([Cl:28])([Cl:29])[Cl:30])=[CH:22][CH:23]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 440266(R)-OctopamineHCID 517044Potassium AcetateHCID 19847900HCID 19847900, compound

Product 1

HCID 178482828HCID 178482828, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 160 ml of acetonitrile were added 32.6 g of N-methanesulfonyl-N'-[2-[[5-[N-methyl-N-(trichloroacetyl)aminomethyl]-2-furyl]methylthio]ethyl]-O-phenylisourea, 13.8 g of DL-octopamine, 21 ml of triethylamine and 2.94 g of potassium acetate. The mixture was refluxed for 1 hour in a nitrogen atmosphere. After cooling, the solvent was removed by distillation under reduced pressure. To the residue thus obtained were added 250 ml of ethyl acetate and 150 ml of water. The mixture was adjusted to pH 2.0 with 2N hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant: benzene:ethyl acetate=1:2) to obtain 29.9 g (yield: 83%) of N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N'-methanesulfonyl-N"-[2-[[5-[N-methyl-N-(trichloroacetyl)aminomethyl]-2-furyl]methylthio]ethyl]guanidine.

Workup

  1. temperatureThe mixture was refluxed for 1 hour in a nitrogen atmosphere
  2. temperatureAfter cooling
  3. customthe solvent was removed by distillation under reduced pressure
  4. customTo the residue thus obtained
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by a column chromatography (eluant: benzene:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-73f358dc3a0044dd99df1fbafbfec0de
Source dataset
uspto-grants-1989_10
Patent number
US04871765

Reaction notes

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