Triethylamine → N-[(1,2-Dihydro-2-oxo-3-pyridinyl)carbonyl]-L-alanyl-L-proline ethyl ester

HRID 1647387ノート

反応式

HRID 1647387 の反応式
Cl.[CH2:2]([O:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13])[CH3:3].C(N(CC)CC)C.[OH:24][C:25]1[N:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>O1CCOCC1.C(Cl)(Cl)Cl>[CH2:2]([O:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH:13][C:27]([C:26]1[C:25](=[O:24])[NH:33][CH:32]=[CH:31][CH:30]=1)=[O:28])[CH3:3]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 15927166L-alanyl-L-proline ethyl ester hydrochlorideHCID 178521113HCID 178521113、化合物

生成物 1

HCID 9862536N-[(1,2-Dihydro-2-oxo-3-pyridinyl)carbonyl]-L-alanyl-L-proline ethyl ester収率 63.4%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

To a stirred solution of 4.0 g (0.016 mol) of L-alanyl-L-proline ethyl ester hydrochloride and 8 ml triethylamine in 200 ml dioxane, maintained at room temperature, a suspension of 3.0 g (0.019 mol) 2-hydroxynicotinoyl chloride in 200 ml anhydrous dioxane is added dropwise over 1 hour. After stirring for a further 3 hours at room temperature, the solvent is distilled off under reduced pressure. The crude product thus obtained is dissolved in 500 ml of chloroform and the solution washed twice with 100 ml of 5% aqueous sodium carbonate. After drying the organic layer over anhydrous magnesium sulfate, the solvent is removed on a rotary evaporator. The solid crystallizes from methylene chloride/isopropyl ether to give 3.4 g of the title compound as a white microcrystalline solid (yield: 64%).

後処理

  1. additionis added dropwise over 1 hour
  2. distillationthe solvent is distilled off under reduced pressure
  3. customThe crude product thus obtained
  4. washthe solution washed twice with 100 ml of 5% aqueous sodium carbonate
  5. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  6. customthe solvent is removed on a rotary evaporator
  7. customThe solid crystallizes from methylene chloride/isopropyl ether

出典と根拠

ORDレコード
ord-c0ebbc4a0f2e464695be431d2e6d3b24
出典データセット
uspto-grants-1995_07
特許番号
US05432159

反応ノート

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