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

HRID 1388108ノート

反応式

HRID 1388108 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2559fd37938341e88b4fb8541a76b055
出典データセット
uspto-grants-1984_02
特許番号
US04430265

反応ノート

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