Triethylamine → N-(2-hydroxy-4-methylphenyl)-3-(tert-butoxycarbonyl)aminopropionamide

HRID 1741540

반응식

HRID 1741540 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:37])=[CH:34][C:35]=1[OH:36].C(N(CC)CC)C>CO.C(Cl)(Cl)Cl.C(OCC)(=O)C>[OH:36][C:35]1[CH:34]=[C:33]([CH3:37])[CH:32]=[CH:31][C:30]=1[NH:29][C:11](=[O:13])[CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 760822-Amino-5-methylphenolHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanine

생성물 1

HCID 19010153N-(2-hydroxy-4-methylphenyl)-3-(tert-butoxycarbonyl)aminopropionamide수율 22%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매2회HCID 21584188Chloroform methanol용매

실험 절차

To 50 ml of ethyl acetate, there were added 4.61 g (24.4 mmol) of N-(tert-butoxycarbonyl)-β-alanine and 5.03 g (24.4 mmol) of N,N'-dicyclohexyl carbodiimide and stirred at room temperature for 30 minutes. To the solution thus obtained, there were added 3.00 g (24.4 mmol) of 6-amino-m-cresol and 2.51 g (24.4 mmol) of triethylamine and stirred at room temperature for 17 hours. After the completion of the reaction, 100 ml of ethyl acetate was added to the solution. After filtering insoluble crystals, the filtrate was washed with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt and dried over anhydrous Glauber's salt. After distilling off the solvent under reduced pressure, the brown solid thus obtained was subjected to silica gel column chromatography (Si60 manufactured by Merck; 230-400 mesh; 300 g; eluent: 5% methanol-chloroform). After distilling off the solvent from the 600-1,200 ml fraction under reduced pressure, pale brown crystals were obtained. These crystals were recrystallized from chloroform and thus 1.56 g (5.3 mmol) of N-(2-hydroxy-4-methylphenyl)-3-(tert-butoxy-carbonyl)aminopropionamide was obtained as pale brown crystals. The yield was 22%.

후처리

  1. customTo the solution thus obtained
  2. stirringstirred at room temperature for 17 hours
  3. additionwas added to the solution
  4. filtrationAfter filtering insoluble crystals
  5. washthe filtrate was washed with 1N hydrochloric acid
  6. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt and dried over anhydrous Glauber's salt
  7. distillationAfter distilling off the solvent under reduced pressure
  8. customthe brown solid thus obtained
  9. distillationAfter distilling off the solvent from the 600-1,200 ml fraction under reduced pressure
  10. custompale brown crystals were obtained
  11. customThese crystals were recrystallized from chloroform

출처 및 근거

ORD 기록
ord-0571cab98cd2496eb661f4493236f9f3
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334225

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