Hydrochloric Acid → (2S)-1-[N-(4-Chlorobenzylaminocarbonyl)-L-prolyl]-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]pyrrolidine

HRID 1720513노트

반응식

HRID 1720513 반응식
ClC(OC(Cl)(Cl)Cl)=O.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.Cl.ClC1C=CC(OCC([C@@H]2CCCN2C(=O)[C@@H]2CCCN2)O)=CC=1.C([O:46][C:47]([N:49]1[CH2:71][CH2:70][CH2:69][C@H:50]1[C:51]([N:53]1[CH2:57][CH2:56][CH2:55][C@H:54]1[CH:58]([OH:68])[CH2:59][O:60][C:61]1[CH:66]=[CH:65][C:64]([Cl:67])=[CH:63][CH:62]=1)=[O:52])=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1.C(Cl)Cl.C(N(CC)CC)C>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][C:47]([N:49]2[CH2:71][CH2:70][CH2:69][C@H:50]2[C:51]([N:53]2[CH2:57][CH2:56][CH2:55][C@H:54]2[CH:58]([OH:68])[CH2:59][O:60][C:61]2[CH:62]=[CH:63][C:64]([Cl:67])=[CH:65][CH:66]=2)=[O:52])=[O:46])=[CH:12][CH:11]=1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 10426DiphosgeneHCID 660364-ChlorobenzylamineHCID 67771535(2S)-1-[N-(tert-butoxycarbonyl)-L-prolyl]-2-[2-(4-chlorophenoxy)-l-hydroxyethyl]pyrrolidineHCID 67771646(2S)-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]-1-(L-prolyl)pyrrolidine hydrochloride

생성물 1

HCID 67771067(2S)-1-[N-(4-Chlorobenzylaminocarbonyl)-L-prolyl]-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]pyrrolidine

시약·촉매·용매 4

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매2회HCID 312751,4-Dioxane용매

실험 절차

To a solution of trichloromethyl chloroformate (0.35 ml) THF (40 ml) was dropwise added a solution of 4-chlorobenzylamine (0.71 ml) and triethylamine (0.81 ml) in THF (20 ml) under ice-cooling, and the mixture was stirred at room temperature for 1.5 hours. A suspension of (2S)-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]-1-(L-prolyl)pyrrolidine hydrochloride which had been obtained by treating (2S)-1-[N-(tert-butoxycarbonyl)-L-prolyl]-2-[2-(4-chlorophenoxy)-l-hydroxyethyl]pyrrolidine (2.13 g) with 4N hydrochloric acid in 1,4-dioxane (20 ml), and triethylamine (0.81 ml) in methylene chloride (20 ml) was dropwise added to the reaction mixture, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 2.09 g of the title compound.

후처리

  1. temperaturecooling
  2. customhad been obtained
  3. additionwas dropwise added to the reaction mixture
  4. stirringby stirring at room temperature for 1 hour
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

출처 및 근거

ORD 기록
ord-8396440d29674d1992a6c27d4a990e63
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05506256

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