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

HRID 1647387노트

반응식

HRID 1647387 반응식
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]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 15927166L-alanyl-L-proline ethyl ester hydrochlorideHCID 178521113HCID 178521113, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 312751,4-Dioxane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c0ebbc4a0f2e464695be431d2e6d3b24
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05432159

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