Hydrochloric Acid → 3,4-di-O-nicotinoyl-N-carbobenzoxydopamine

HRID 5906

반응식

HRID 5906 반응식
[C:1]([NH:11][CH2:12][CH2:13][C:14]1[CH:21]=[CH:20][C:18]([OH:19])=[C:16]([OH:17])[CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1>N1C=CC=CC=1>[C:23]([O:17][C:16]1[CH:15]=[C:14]([CH:21]=[CH:20][C:18]=1[O:19][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1)[CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 82604Nicotinoyl chlorideHCID 11108946Benzyl N-[2-(3,4-dihydroxyphenyl)ethyl]carbamate

생성물 1

HCID 1317181713,4-di-O-nicotinoyl-N-carbobenzoxydopamine수율 71.6%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

19.0 g (66 mmol) of N-carbobenzoxydopamine obtained in Synthetic Example 1-(1) and 37.2 g (209 mmol) of hydrochloride of nicotinoyl chloride were added to 200 ml of pyridine. After stirring at room temperature for 12 hours, the mixture was allowed to react at 35°-40° C. for 2 hours. Then, the reaction mixture was poured into ice and a sodium carbonate solution followed by extraction with chloroform. The resulting extract was dried over anhydrous magnesium sulfate and the solvent was distilled off to obtain crude crystals. The thus-obtained crystals were recrystallized from ethyl acetate/diethyl ether (1:5 by volume) to obtain 23.5 g (yield: 71.6%) of the desired compound in the form of white crystals (m.p. 77°-78° C.).

후처리

  1. customto react at 35°-40° C. for 2 hours
  2. additionThen, the reaction mixture was poured into ice
  3. extractiona sodium carbonate solution followed by extraction with chloroform
  4. extractionThe resulting extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customto obtain crude crystals
  8. customThe thus-obtained crystals were recrystallized from ethyl acetate/diethyl ether (1:5 by volume)

출처 및 근거

ORD 기록
ord-904e0eff30db466b8a5980cfec8f75e8
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246949

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