Dicyclohexylcarbodiimide → HCID 67874023、化合物

HRID 1418692ノート

反応式

HRID 1418692 の反応式
[CH3:1][C:2]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:6])[C:3]([OH:5])=[O:4].C1(N=C=NC2CCCCC2)CCCCC1.O[CH:31]([C:34]1[CH:50]=[C:49]2[N:37]([CH2:38][C:39]3[C:40]2=[N:41][C:42]2[C:47]([CH:48]=3)=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36](=[O:51])[C:35]=1[CH3:52])[CH2:32][CH3:33]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:52][C:35]1[C:36](=[O:51])[N:37]2[C:49](=[CH:50][C:34]=1[CH:31]([O:4][C:3](=[O:5])[C:2]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:1])[CH3:6])[CH2:32][CH3:33])[C:40]1=[N:41][C:42]3[C:47]([CH:48]=[C:39]1[CH2:38]2)=[CH:46][CH:45]=[CH:44][CH:43]=3

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 613105HCID 613105、化合物HCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

生成物 1

HCID 67874023HCID 67874023、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture containing 2-methyl-2-[N-[(1,1-dimethylethoxy)carbonyl]amino]propionic acid (406 mg, 2.0 mmol) and dicyclohexylcarbodiimide (432 mg, 2.0 mmol) in CH2Cl2 (3 mL) under an argon atmosphere were added (±)-7-(1-hydroxypropyl)-8-methylindolizino[1,2-b]quinolin-9(11H)-one (153 mg, 0.5 mmol) and 4-dimethylaminopyridine (25 mg). The resulting mixture was allowed to stir at room temperature for 4 d and then was poured into CH2Cl2, washed successively with 5% aqueous NaHCO3, 0.5N HCl and H2O, and dried over sodium sulfate. Removal of the solvent in vacuo and purification of the residue by column chromatography (silica gel) eluting with a solvent gradient of 1.5-5% MeOH/CH2Cl2 afforded the title compound as an off-white solid. 1H NMR (CDCl3) d 8.33 (s, 1H), 8.20 (d, J=8.9 Hz, 1H), 7.90 (d, J=8.3 Hz, 1H), 7.80 (m, 1H), 7.62 (m, 1H), 7.33 (s, 1H), 5.92 (dd, J=7.5, 6.3 Hz, 1H), 5.25 (s, 2H), 5.10 (br s, 1H), 2.38 (s, 3H), 2.08-1.82 (m, 2H), 1.56 (s, 3H), 1.55 (s, 3H), 1.41 (s, 9H), 0.99 (t, J=7.4 Hz, 3H).

後処理

  1. washwashed successively with 5% aqueous NaHCO3, 0.5N HCl and H2O
  2. dry with materialdried over sodium sulfate
  3. customRemoval of the solvent
  4. customin vacuo and purification of the residue by column chromatography (silica gel)
  5. washeluting with a solvent gradient of 1.5-5% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-fb84cae122dc46eda2d56ca6b666ec51
出典データセット
uspto-grants-1999_03
特許番号
US05883255

反応ノート

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