Triethylamine → N-(2-ethoxy-2-oxoethyl)-N-[1,2-dioxo-2-[4-[(12-phenoxydodecyl)oxy] phenyl]ethyl]glycine ethyl ester

HRID 488334ノート

反応式

HRID 488334 の反応式
[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:8][CH:7]=1)[C:3]([OH:5])=O.C(Cl)(=O)C(Cl)=O.[NH:38]([CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH2:43]([O:42][C:40](=[O:41])[CH2:39][N:38]([CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])[C:3](=[O:5])[C:2](=[O:1])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:8][CH:7]=1)[CH3:44]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 80502Diethyl iminodiacetateHCID 19091785alpha-Oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid

生成物 1

HCID 19091810N-(2-ethoxy-2-oxoethyl)-N-[1,2-dioxo-2-[4-[(12-phenoxydodecyl)oxy] phenyl]ethyl]glycine ethyl ester収率 84.9%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To 1.12 g (2.6 mmol) of alpha-oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid in 50 ml of methylene chloride containing 2 drops of anhydrous DMF stirred and cooled in an ice bath was added 1.1 ml (13 mmol) of oxalyl chloride. The cooling bath was removed and stirring was continued at room temperature for 1.5 hours. The solvent was removed at reduced pressure and the resultant solid acid chloride was dissolved in 50 ml of methylene chloride and added dropwise to a stirred, ice bath cooled solution of 0.7 ml (5.25 mmol) of diethyl iminodiacetate and 0.7 ml (5.25 mmol) of triethylamine in 15 ml of methylene chloride. The reaction mixture was stirred at room temperature for 16 hours and then was concentrated at reduced pressure. The resultant crude product was triturated with methanol and filtered to give 1.32 g (84% yield, mp 55°-56°) of N-(2-ethoxy-2-oxoethyl)-N-[1,2-dioxo-2-[4-[(12-phenoxydodecyl)oxy] phenyl]ethyl]glycine ethyl ester. The nmr and mass spectra were consistent with the structure.

後処理

  1. temperaturecooled in an ice bath
  2. customThe cooling bath was removed
  3. customThe solvent was removed at reduced pressure
  4. dissolutionthe resultant solid acid chloride was dissolved in 50 ml of methylene chloride
  5. additionadded dropwise to a stirred, ice bath
  6. stirringThe reaction mixture was stirred at room temperature for 16 hours
  7. concentrationwas concentrated at reduced pressure
  8. customThe resultant crude product was triturated with methanol
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-4fd3ce71372a4731a9532e6041fa9692
出典データセット
uspto-grants-1994_03
特許番号
US05298652

反応ノート

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