Hydrochloric Acid → 3-benzyloxyacetylamino-4-benzyloxy-alpha-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl]benzyl alcohol

HRID 1731095

Reaction equation

HRID 1731095 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:5]([OH:25])[CH2:6][N:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:8]([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[CH2:37]([O:44][CH2:45][C:46](Cl)=[O:47])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[OH-].[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C.C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:37]([O:44][CH2:45][C:46]([NH:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH:5]([OH:25])[CH2:6][N:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:8]([CH3:17])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)=[O:47])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 177085Benzyloxyacetyl chlorideHCID 539014743-amino-4-benzyloxy-alpha-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)-aminomethyl]benzyl alcohol

Product 1

HCID 542780313-benzyloxyacetylamino-4-benzyloxy-alpha-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl]benzyl alcohol

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

In 20 ml. of anhydrous pyridine there was dissolved 2 g. of 3-amino-4-benzyloxy-α-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)-aminomethyl]benzyl alcohol (prepared in the aforesaid Reference Example 7-a) and the solution was cooled to temperatures from -20° to -30° C. A solution of 2.28 g. of benzyloxyacetyl chloride in 5 ml. of toluene was added dropwise to the solution thus cooled and while stirring the mixture, the temperature of the mixture was elevated slowly to room temperature. After stirring the mixture overnight, the solvent was distilled off under reduced pressure and the residue was mixed with 50 ml. of water. After washing the benzene solution thus obtained with water, benzene was distilled off from the reaction mixture under reduced pressure to provide a red oily material. The product was dissolved in 50 ml. of ethanol and after adding to the solution 5 ml. of water and 10 ml. of 4N sodium hydroxide solution, the resultant mixture was stirred for two hours. After adjusting the pH of the reaction mixture to 3 by adding 1N hydrochloric acid, an excessive amount of sodium carbonate was added thereto. Then, ethanol was distilled off under reduced pressure and the residue was extracted with benzene. The extract was washed three times with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide a yellow oily material. The product was then subjected to a silica gel column chromatography (65 ml.). The product was eluted using 9 : 1 benzene-acetone mixture and the effluent was concentrated under reduced pressure to provide 3-benzyloxyacetylamino-4-benzyloxy-α-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl]benzyl alcohol.

Workup

  1. temperaturewas cooled to temperatures from -20° to -30° C
  2. temperaturethus cooled
  3. customwas elevated slowly to room temperature
  4. stirringAfter stirring the mixture overnight
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionthe residue was mixed with 50 ml
  7. washAfter washing the benzene solution
  8. customthus obtained with water, benzene
  9. distillationwas distilled off from the reaction mixture under reduced pressure
  10. customto provide a red oily material
  11. dissolutionThe product was dissolved in 50 ml
  12. distillationThen, ethanol was distilled off under reduced pressure
  13. extractionthe residue was extracted with benzene
  14. washThe extract was washed three times with water
  15. dry with materialdried over anhydrous sodium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customto provide a yellow oily material
  18. washThe product was eluted
  19. concentrationthe effluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49b7d5fe7c8142c683758391e5226e37
Source dataset
uspto-grants-1976_11
Patent number
US03994974

Linked notes

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