反应 #470381

ord-eafcc244dfa248c5ba85114b659eccac

反应方程式

COC(=O)[C@@H](N)CCCCN.Cl.Cl
L-lysine methyl ester dihydrochloride
CCN(CC)CC
triethylamine
O=C(Cl)COCc1ccccc1
benzyloxy acetyl chloride
COC(=O)C(CCCCNC(=O)COCc1ccccc1)NC(=O)COCc1ccccc1
2
收率 31.8%
COC(=O)C(CCCCNC(=O)COCc1ccccc1)NC(=O)COCc1ccccc1
2,6-Bis-(2-benzyloxy-acetylamino)-hexanoic acid methyl ester
收率 31.8%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    过滤The solids were filtered off
  2. 2
    洗涤The organic phase was washed with 5% sodium bicarbonate (2×100 mL), water (2×100 mL)
  3. 3
    干燥dried over sodium sulphate
  4. 4
    workup.DISTILLATIONdistilled
  5. 5
    其他The crude 2 was purified by column chromatography on silica gel

实验过程

To a mixture of L-lysine methyl ester dihydrochloride (50 grams, 214.4 mmol), triethylamine (131 grams, 1.294 moles) in ethyl acetate (750 mL) at room temperature was added benzyloxy acetyl chloride (120 grams, 650.4 mmol) drop wise. The mixture was further stirred at room temperature for 2 hours. The solids were filtered off. The organic phase was washed with 5% sodium bicarbonate (2×100 mL), water (2×100 mL), dried over sodium sulphate and distilled. The crude 2 was purified by column chromatography on silica gel using Benzene: Ethyl acetate (9:1) to get pure 2 (30 grams, 31.8%) as a white powder.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08367108B2uspto-grants-2013_02