Butylamine → (S)-1-benzyloxycarbonyl-N-butyl-2-pyrrolidinecarboxamide

HRID 64820

반응식

HRID 64820 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[CH2:32]([NH2:36])[CH2:33][CH2:34][CH3:35]>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([NH:36][CH2:32][CH2:33][CH2:34][CH3:35])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8007ButylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 101987Benzyloxycarbonyl-L-proline

생성물 1

HCID 13564336(S)-1-benzyloxycarbonyl-N-butyl-2-pyrrolidinecarboxamide수율 70.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

In 50 ml of THF was dissolved 4.99 g of N-benzyloxycarbonyl-L-proline and then 2.23 g of triethylamine was added to the solution. Then, after slowly adding thereto 2.39 g of ethyl chloroformate under ice-cooling, the reaction was maintained for one hour at 0° C. to 5° C. Then, 2.19 g of n-butylamine was slowly added to the reaction mixture under ice-cooling, the reaction was further performed for one hour at 0° C. to 5° C. The solvent was removed from the reaction mixture, the residue thus formed was dissolved in ethyl acetate, and the solution was washed successively with an aqueous solution of 1N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution, and a saturated aqueous sodium chloride solution. The organic layer this formed was collected, dried by Glauber's salt, and then concentrated by dryness. The product was recrystallized from water to provide 4.31 g of (S)-1-benzyloxycarbonyl-N-butyl-2-pyrrolidinecarboxamide (30). M.p. 88°-90° C.

후처리

  1. additionThen, after slowly adding
  2. temperaturethe reaction was maintained for one hour at 0° C. to 5° C
  3. temperaturecooling
  4. customThe solvent was removed from the reaction mixture
  5. customthe residue thus formed
  6. washthe solution was washed successively with an aqueous solution of 1N hydrochloric acid
  7. customThe organic layer this formed was collected
  8. dry with materialdried by Glauber's salt
  9. concentrationconcentrated by dryness
  10. customThe product was recrystallized from water

출처 및 근거

ORD 기록
ord-26facd80d0444cda9e764bbf6f3a0d5c
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04610821

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