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

HRID 1731098

반응식

HRID 1731098 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4301f2397d5f4984bec9e2987cfcaaf6
출처 데이터셋
uspto-grants-1976_11
특허 번호
US03994974

연결된 노트

불러오는 중…