Triethylamine → N-(2-chloro-6-nitrobenzyl)-L-alanine ethyl ester

HRID 127571

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HRID 127571 반응식
Cl.[CH2:2]([O:4][C:5](=[O:9])[C@H:6]([CH3:8])[NH2:7])[CH3:3].C(N(CC)CC)C.Br[CH2:18][C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:28]>C(O)C>[CH2:2]([O:4][C:5](=[O:9])[C@H:6]([CH3:8])[NH:7][CH2:18][C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:28])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 918582-(Bromomethyl)-1-chloro-3-nitrobenzeneHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

생성물 1

HCID 53708925N-(2-chloro-6-nitrobenzyl)-L-alanine ethyl ester수율 91.7%

시약·촉매·용매 1

HCID 702Ethanol용매3회

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온도
80 °C

실험 절차

18.24 g of L-alanine ethyl ester hydrochloride in 60 ml of ethanol was added dropwise to a mixture of 25 ml of triethylamine in 60 ml of ethanol and the mixture was heated to 80° C. The resulting solution was added dropwise at this temperature to a solution of 15 g of α-bromo-2-chloro-6-nitrotoluene in 60 ml of ethanol. The mixture was stirred at 80° C. overnight and then evaporated to dryness. The residue was treated with 150 ml of deionised water and extracted twice with 100 ml of methylene chloride. The methylene chloride extracts were washed with water, dried and evaporated. The resulting product was purified by chromatography on silica gel with methylene chloride/5% methanol. There were obtained 15.75 g (91% of theory) of N-(2-chloro-6-nitrobenzyl)-L-alanine ethyl ester; nD20 =1.5267.

후처리

  1. customevaporated to dryness
  2. additionThe residue was treated with 150 ml of deionised water
  3. extractionextracted twice with 100 ml of methylene chloride
  4. washThe methylene chloride extracts were washed with water
  5. customdried
  6. customevaporated
  7. customThe resulting product was purified by chromatography on silica gel with methylene chloride/5% methanol

출처 및 근거

ORD 기록
ord-b36b9db07ec04c54a12306153c9f1ab9
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04256748

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