Dicyclohexylcarbodiimide → 3-(N-acetyl-beta-alanyl)amino-4-benzyloxy-alpha-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl]benzyl alcohol

HRID 1731098

Reaction equation

HRID 1731098 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:6]([OH:26])[CH2:7][N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:9]([CH3:18])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[C:38]([NH:41][CH2:42][CH2:43][C:44](O)=[O:45])(=[O:40])[CH3:39].C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[C:38]([NH:41][CH2:42][CH2:43][C:44]([NH:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH:6]([OH:26])[CH2:7][N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:9]([CH3:18])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)=[O:45])(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 76406N-Acetyl-beta-alanineHCID 681367333-amino-4-benzyloxy-alpha-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)-aminomethyl]benzyl alcohol hydrochloride

Product 1

HCID 540507863-(N-acetyl-beta-alanyl)amino-4-benzyloxy-alpha-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl]benzyl alcohol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 30 ml. of anhydrous pyridine there were dissolved 4g. of 3-amino-4-benzyloxy-α-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)-aminomethyl]benzyl alcohol hydrochloride and 3.5 g of N-acetyl-β-alanine and after adding to the solution 5.5 g. of dicyclohexylcarbodiimide under ice-cooling, the mixture was stirred overnight. After filtering off the precipitates thus formed, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in 30 ml. of methanol. Then, after adding to the solution 10 ml. of 4N sodium hydroxide solution, the mixture was stirred for 3 hours and further after adding thereto 1N hydrochloric acid solution to adjust the pH to 3 and adding excessive sodium carbonate, the resultant mixture was stirred for 30 minutes. The reaction product was concentrated under a reduced pressure and then extracted with 50 ml. of chloroform. The extract was washed three times with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to five 4 g. of a yellow oily material. By subjecting the product to a silica gel column chromatography (75 ml.) and further to a silica gel column chromatography (35 ml.), 800 mg. of a pure caramel-like 3-(N-acetyl-β-alanyl)amino-4-benzyloxy-α-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl]benzyl alcohol was obtained. In the above chromatographic purification treatments, 4 : 2 : 1 ethyl acetate-benzene-methanol was used as the developing solvent.

Workup

  1. filtrationAfter filtering off the
  2. customprecipitates thus
  3. customformed
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in 30 ml
  6. additionThen, after adding to the solution 10 ml
  7. stirringof 4N sodium hydroxide solution, the mixture was stirred for 3 hours
  8. additionfurther after adding
  9. additionadding excessive sodium carbonate
  10. stirringthe resultant mixture was stirred for 30 minutes
  11. concentrationThe reaction product was concentrated under a reduced pressure
  12. extractionextracted with 50 ml
  13. washThe extract was washed three times with water
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationconcentrated under reduced pressure to five 4 g

Sources & evidence

ORD record
ord-4301f2397d5f4984bec9e2987cfcaaf6
Source dataset
uspto-grants-1976_11
Patent number
US03994974

Linked notes

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