تفاعل #470381

ord-eafcc244dfa248c5ba85114b659eccac

معادلة التفاعل

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
المردود 31.8%
COC(=O)C(CCCCNC(=O)COCc1ccccc1)NC(=O)COCc1ccccc1
2,6-Bis-(2-benzyloxy-acetylamino)-hexanoic acid methyl ester
المردود 31.8%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe solids were filtered off
  2. 2
    غسيلThe organic phase was washed with 5% sodium bicarbonate (2×100 mL), water (2×100 mL)
  3. 3
    تجفيفdried over sodium sulphate
  4. 4
    workup.DISTILLATIONdistilled
  5. 5
    أخرىThe crude 2 was purified by column chromatography on silica gel

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08367108B2uspto-grants-2013_02