Triethylamine → HCID 14720611、化合物

HRID 477868

反応式

HRID 477868 の反応式
[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.Cl.[CH3:17][O:18][C:19](=[O:28])[C@H:20]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[NH2:21].C(N(CC)CC)C>CN(C)C=O.CN(C)C1C=CN=CC=1.C(Cl)Cl.C1C=CC=CC=1>[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:21][C@H:20]([C:19]([O:18][CH3:17])=[O:28])[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:6]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27745162-Fluoro-4-iodobenzoic acidHCID 12917568Dimethyl L-glutamate hydrochloride

生成物 1

HCID 14720611HCID 14720611、化合物収率 74%

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 142844-(Dimethylamino)pyridine触媒HCID 241Benzene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To 20 mL of benzene are added 2.0 g (0.00752 mol) of 2-fluoro4-iodobenzoic acid, followed by 2.3 mL (320 mmol) of thionyl chloride and several drops of dimethylformamide. The mixture is heated at reflux of 3.5 hours. The solvent is then removed in vacuo and the residue pumped dry. The resulting acid chloride is redissolved in 10 ml of methylene chloride, and added dropwise to cooled mixture of 1.67 g (7.89 mmol) of L-glutamic acid dimethyl ester hydrochloride, 5 mg of 4-dimethylaminopyridine, and 2.2 mL (15.8 mmol) of triethylamine in 30 mL of methylene chloride. After the addition, the reaction stirred at room temperature for 18 hours. The reaction mixture is then diluted with additional methylene chloride, washed with 1N hydrochloric acid, water and 5% sodium bicarbonate and dried over sodium sulfate. The solvent is removed in vacuo to give 2.34 g (74%) of dimethyl N-(2-fluoro-4-iodobenzoyl)-L-glutamate as a white solid m.p. 94°-96° C.; IR (KBr, cm-1)=1159, 1177, 1194, 1208, 1229, 1398, 1437, 1477, 1537, 1601, 1642, 1728, 1739, 1756, 3326.

後処理

  1. temperatureThe mixture is heated
  2. temperatureat reflux of 3.5 hours
  3. customThe solvent is then removed in vacuo
  4. customthe residue pumped dry
  5. dissolutionThe resulting acid chloride is redissolved in 10 ml of methylene chloride
  6. additionadded dropwise
  7. temperatureto cooled
  8. additionAfter the addition
  9. washwashed with 1N hydrochloric acid, water and 5% sodium bicarbonate
  10. dry with materialdried over sodium sulfate
  11. customThe solvent is removed in vacuo

出典と根拠

ORDレコード
ord-42430265d92c41e7a5c2bd056593e131
出典データセット
uspto-grants-1989_12
特許番号
US04889859

関連ノート

読み込み中…