Triethylamine → 2-(2-Chloro-phenyl)-4-ethyl-oxazole-5-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

HRID 2236177ノート

反応式

HRID 2236177 の反応式
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=O)=O.C(Cl)(=O)[C:18](Cl)=[O:19].C(N(CC)CC)C.[OH:30][N:31]1[C:35](=[O:36])[CH2:34][CH2:33][C:32]1=[O:37]>O1CCCC1>[O:37]=[C:32]1[CH2:33][CH2:34][C:35](=[O:36])[N:31]1[O:30][C:18]([C:8]1[O:10][C:4]([C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[Cl:1])=[N:6][C:7]=1[CH2:11][CH3:12])=[O:19]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 80170N-HydroxysuccinimideHCID 242068382-(2-Chloro-benzoylamino)-butyric acid

生成物 1

HCID 593013122-(2-Chloro-phenyl)-4-ethyl-oxazole-5-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester収率 25%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a stirred slurry of 2-(2-chloro-benzoylamino)-butyric acid (2.84 g, 11.8 mmol) in 60 mL of anhydrous tetrahydro furan, was added oxalyl chloride (10.1 mL, 118 mmol). The mixture was stirred at 50° C. overnight and then the solvent was evaporated in vacuo. The oily residue was treated with toluene and evaporated to remove trace of oxalyl chloride. The residue was then cooled in an ice bath and triethylamine (3.4 mL, 23.6 mmol) was added followed by the addition of 1-hydroxy-pyrrolidine-2,5-dione. The reaction mixture was stirred at 50° C. overnight before the solvent was removed in vacuo. The residue was then purified by flash chromatography (Merck silica gel 60, 230-400 mesh, 5-60% ethyl acetate in hexane for 25 min) to give 2-(2-chloro-phenyl)-4-ethyl-oxazole-5-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester (997 mg, 25% yield) as a light yellow solid. LCMS calcd for C16H13ClN2O5 (m/e) 348, obsd 349 (M+H).

後処理

  1. customthe solvent was evaporated in vacuo
  2. additionThe oily residue was treated with toluene
  3. customevaporated
  4. customto remove trace of oxalyl chloride
  5. temperatureThe residue was then cooled in an ice bath
  6. stirringThe reaction mixture was stirred at 50° C. overnight before the solvent
  7. customwas removed in vacuo
  8. customThe residue was then purified by flash chromatography (Merck silica gel 60, 230-400 mesh, 5-60% ethyl acetate in hexane for 25 min)

出典と根拠

ORDレコード
ord-34b268a9426c46fbb4704e275f5d2405
出典データセット
uspto-grants-2010_05
特許番号
US07714126B2

反応ノート

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