Sodium triacetoxyborohydride → [[4-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzylamino)-butyl]-propyl-amino]-acetic acid ethyl ester

HRID 2080876노트

반응식

HRID 2080876 반응식
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](OC(C)(C)C)=O)[CH2:7][CH2:8][CH3:9])[CH3:2].Cl.O1CCOCC1.[NH:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH2:35][N:36]([CH2:44][C:45]1[CH:52]=[CH:51][C:48](C=O)=[CH:47][CH:46]=1)[CH2:37][C:38]1[N:39]([CH3:43])[CH:40]=[CH:41][N:42]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C.C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([CH2:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][C:48]1[CH:51]=[CH:52][C:45]([CH2:44][N:36]([CH2:35][C:31]2[NH:30][CH:34]=[CH:33][N:32]=2)[CH2:37][C:38]2[N:39]([CH3:43])[CH:40]=[CH:41][N:42]=2)=[CH:46][CH:47]=1)[CH2:7][CH2:8][CH3:9])[CH3:2]

참가 물질

7

반응물 4

HCID 5049666Sodium triacetoxyborohydrideHCID 204431481,4-Dioxane hydrochloride2회HCID 86614915[(4-t-Butoxycarbonylamino-butyl)-propyl-amino]-acetic acid ethyl esterHCID 866149184-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzaldehyde

생성물 1

HCID 67103519[[4-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzylamino)-butyl]-propyl-amino]-acetic acid ethyl ester수율 56%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 702Ethanol용매3회

실험 절차

The compound (273.0 mg) obtained in Example 84-2 was dissolved in ethanol (2.7 ml) and added with a 4 mol/l hydrogen chloride/dioxane solution (2.7 ml) and the whole was stirred at room temperature for 1 hour. Further, the solution was added with a 4 mol/l hydrogen chloride/dioxane solution (1.0 ml) and the whole was stirred at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off, thereby obtaining a crude product (350.0 mg) of [(4-amino-butyl)-propyl-amino]-acetic acid ethyl ester as a colorless oily substance. The resultant crude product (350.0 mg) was dissolved in ethanol (4.5 ml) and added with an ethanol solution (2.6 ml) containing the compound (258 mg) obtained in Example 84-5, acetic acid (0.10 ml), and sodium triacetoxyborohydride (267.0 mg) and the whole was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (238.0 mg) as a pale-yellow oily substance.

후처리

  1. stirringthe whole was stirred at room temperature for 30 minutes
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. customobtaining a crude product (350.0 mg) of [(4-amino-butyl)-propyl-amino]-acetic acid ethyl ester as a colorless oily substance
  5. stirringthe whole was stirred at room temperature for 2 hours
  6. customAfter completion of the reaction
  7. distillationthe solvent was distilled off
  8. dissolutionThe residue was dissolved in chloroform
  9. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  10. extractionfollowed by extraction with chloroform
  11. washThe organic layer was washed with a saturated saline solution
  12. dry with materialdried with anhydrous sodium sulfate
  13. filtrationAfter filtration
  14. distillationthe solvent was distilled off
  15. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-4fe8b8e0f8a54c4fb99a618cd9563b81
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932281B2

반응 노트

불러오는 중…