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

HRID 583105Notes

Reaction equation

HRID 583105 reaction equation
[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

Participants

6

Reactant 5

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7571a2ace8a9401cbf9fe57f1c1d5355
Source dataset
uspto-grants-1999_07
Patent number
US05929074

Reaction notes

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