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

HRID 1741540ノート

反応式

HRID 1741540 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒2 回HCID 21584188Chloroform methanol溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-0571cab98cd2496eb661f4493236f9f3
出典データセット
uspto-grants-1994_08
特許番号
US05334225

反応ノート

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