Acetic Acid → benzyl (2R)-2-[4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]propionate

HRID 1489415노트

반응식

HRID 1489415 반응식
[F:1][C:2]([F:20])([CH:17]([F:19])[F:18])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[N:14][NH:13][C:12]2=[O:16])=[CH:7][CH:6]=1.FC(F)(F)S(O[C@@H:27]([CH3:38])[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])(=O)=O.C(O)(=O)C>CN(C)C=O.[H-].[Na+].O1CCCC1.C(OCC)(=O)C.C(OC(C)C)(C)C>[F:20][C:2]([F:1])([CH:17]([F:19])[F:18])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:12](=[O:16])[N:13]([C@H:27]([CH3:38])[C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])[N:14]=[CH:15]2)=[CH:7][CH:6]=1

참가 물질

9

반응물 3

HCID 176Acetic AcidHCID 10779907HCID 10779907, 화합물HCID 10881508Phenylmethyl (2S)-2-[[(trifluoromethyl)sulfonyl]oxy]propanoate

생성물 1

HCID 10694967benzyl (2R)-2-[4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]propionate수율 85.6%

시약·촉매·용매 5

HCID 6228Dimethylformamide용매HCID 7914Diisopropyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 24758Sodium hydride용매

실험 절차

4-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (18 g) was dissolved in 180 ml of dimethylformamide, to which 60% sodium hydride in oil (2.52 g) was added. The mixture was vigorously stirred at room temperature for 40 minutes. The reaction solution was added to a solution of 20 g of benzyl (2S)-2-trifluoromethanesulfonyloxypropionate prepared in Example 3 in 240 ml of tetrahydrofuran under nitrogen atmosphere at -40° to -30° C. over the period of ca. 40 minutes. The mixture was stirred at -40° to -20° C. for 40 minutes, to which 10 ml of acetic acid was added. Then, the reaction solution was diluted with a mixture of 100 ml of ethyl acetate and 500 ml of diisopropyl ether, washed with 250 ml of water, 2N-hydrochloric acid (250 ml×2) and 250 ml of an aqueous solution of sodium chloride successively. After dring over magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 250 g, eluent; hexane:ethyl acetate=2:1) to give 24 g of benzyl (2R)-2-[4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]propionate (yield: 82%) as a colorless oil.

후처리

  1. additionwas added
  2. additionwas added
  3. washwashed with 250 ml of water, 2N-hydrochloric acid (250 ml×2) and 250 ml of an aqueous solution of sodium chloride successively
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography (silica gel: 250 g, eluent; hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-0e9491efff11447b8873c584ef7f8c42
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05677464

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