4-Nitrophenol → N-carbobenzoxy-11-aminoundecanoic acid p-nitrophenyl ester

HRID 1388108노트

반응식

HRID 1388108 반응식
[C:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH:25]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[C:27](O)[CH:26]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.CN(C)C=O>[N+:31]([C:30]1[CH:25]=[CH:26][C:27]([O:23][C:22](=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])=[CH:28][CH:29]=1)([O-:33])=[O:32]

참가 물질

6

반응물 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 56228011-(((Benzyloxy)carbonyl)amino)undecanoic acid

생성물 1

HCID 12086735N-carbobenzoxy-11-aminoundecanoic acid p-nitrophenyl ester수율 55.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

In a solvent mixture (120 ml) of ethyl acetate and N,N-dimethylformamide (5:1) was dissolved N-carbobenzoxy-11-aminoundecanoic acid (10.1 g, 30 m mols) and p-nitrophenol (4.59 g, 33 m mols), followed by addition of N,N'-dicyclohexylcarbodiimide (6.80 g, 33 m mols). The mixture was stirred at room temperature for 15 hours, after which the precipitate was filtered off. The solvent was distilled off and the residue was crystallized in petroleum ether, recovered by filtration and recrystallized from ethyl acetate-petroleum ether. By the above procedure there was obtained 7.65 g of N-carbobenzoxy-11-aminoundecanoic acid p-nitrophenyl ester. m.p. 72°-73° C.; Rf1 =0.94.

후처리

  1. filtrationafter which the precipitate was filtered off
  2. distillationThe solvent was distilled off
  3. customthe residue was crystallized in petroleum ether
  4. filtrationrecovered by filtration
  5. customrecrystallized from ethyl acetate-petroleum ether

출처 및 근거

ORD 기록
ord-2559fd37938341e88b4fb8541a76b055
출처 데이터셋
uspto-grants-1984_02
특허 번호
US04430265

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