Tetrahydrofuran → N-Benzyloxycarbonyl-3-(4-methylpiperazin-1-yl)-carbonylmethoxy-4-methoxybenzylamine

HRID 583105ノート

反応式

HRID 583105 の反応式
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15](OCC(O)=O)[CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC([O:36][CH2:37][CH3:38])=O.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.[O:46]1CCCC1>>[CH2:1]([O:8][C:9]([N:11]([O:46][CH:38]=[C:37]=[O:36])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([N:43]2[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]2)[CH:14]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 5

HCID 8028Tetrahydrofuran3 回HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 531671-MethylpiperazineHCID 19689422N-Benzyloxycarbonyl-3-carboxymethyloxy-4-methoxybenzylamine

生成物 1

HCID 54104530N-Benzyloxycarbonyl-3-(4-methylpiperazin-1-yl)-carbonylmethoxy-4-methoxybenzylamine

実験手順

A mixture comprising 5 g of N-benzyloxycarbonyl-3-carboxymethyloxy-4-methoxybenzylamine, 1.67 g of triethylamine and 40 ml of tetrahydrofuran, was cooled with ice, and 1.79 g of ethyl chloroformate dissolved in 10 ml of tetrahydrofuran, was dropwise added thereto. The mixture was stirred for 2 hours. Then, 1.65 g of methylpiperazine dissolved in 10 ml of tetrahydrofuran, was added to the reaction solution, and the mixture was stirred at room temperature for 4.5 hours. The precipitate was filtered off, and the filtrate was distilled under reduced pressure. Water was added to the obtained residue, and the mixture was extracted with chloroform. The extract solution was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The obtained residue was crystallized from ethyl acetate/diethyl ether/n-hexane to obtain 3.53 g of the above-identified compound as white crystals.

後処理

  1. additionwas dropwise added
  2. additionwas added to the reaction solution
  3. stirringthe mixture was stirred at room temperature for 4.5 hours
  4. filtrationThe precipitate was filtered off
  5. distillationthe filtrate was distilled under reduced pressure
  6. additionWater was added to the obtained residue
  7. extractionthe mixture was extracted with chloroform
  8. washThe extract solution was washed with water
  9. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  10. distillationThen, the solvent was distilled off
  11. customThe obtained residue was crystallized from ethyl acetate/diethyl ether/n-hexane

出典と根拠

ORDレコード
ord-7571a2ace8a9401cbf9fe57f1c1d5355
出典データセット
uspto-grants-1999_07
特許番号
US05929074

反応ノート

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