Oxygen → N,N'-Dicyclohexylurea

HRID 1277729ノート

反応式

HRID 1277729 の反応式
[OH:1]N1C2C=CC=CC=2N=N1.[CH:11]1([N:17]=[C:18]=[N:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.O=O.C1C=C2C(O)=CNC2=CC=1.C(N(CC)CC)C>O.O1CCCC1>[CH:20]1([NH:19][C:18]([NH:17][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[O:1])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

参加物

8

反応物 5

HCID 977OxygenHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 50591IndoxylHCID 757711-Hydroxybenzotriazole

生成物 1

HCID 4277N,N'-Dicyclohexylurea

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

For the reaction by the active ester process, 4.26 g. (0.02 mol) N-(furyl-(2')-methoxycarbonyl)-L-alanine and 5.4 g. (0.04 mol) N-hydroxybenzotriazole are dissolved in 50 ml. anhydrous tetrahydrofuran (THF), cooled to 0° C. and mixed with a solution of 4.4 g. (0.022 mol) dicyclohexylcarbodiimide (DCC) in 10 ml. anhydrous THF. For the formation of the active ester, the reaction mixture is stirred for 1.5 hours at 0° C. and then for 2 hours at ambient temperature. Thereafter, with the exclusion of oxygen and water, there are added thereto 2.66 g. (0.02 mol) indoxyl and 2.77 ml. (0.04 mol) anhydrous triethylamine. The reaction mixture is stirred for 18 hours at ambient temperature. The N,N'-dicyclohexylurea formed is filtered off with suction, the solvent is distilled off in a vacuum and the residue is worked up in the manner described in Example 7. The amorphous crude product obtained is then purified by column chromatography on a silica gel column with a mixture of toluene and ethyl acetate (5:1 v/v). After evaporation of the appropriate collected fractions and recrystallization of the residue from ethyl acetate-petroleum ether (1:1 v/v), there are obtained 3.0 g. (45.7% of theory) 3-[N-(furyl-(2')-methoxycarbonyl)-L-alanyloxy]-indole in the form of colorless crystals; m.p. 129° C.: [α]D20 =-51.9° (c=1% in methanol).

後処理

  1. additionmixed with a solution of 4.4 g

出典と根拠

ORDレコード
ord-92f617fb82564ab2b2b2ba8d3769f4ae
出典データセット
uspto-grants-1981_07
特許番号
US04278763

反応ノート

読み込み中…