Triethylamine → (S)-1-benzyloxycarbonyl-N-[3-(2-oxo-pyrrolidinyl)propyl]-2-pyrrolidine carboxamide

HRID 64840

반응식

HRID 64840 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(C)C)=O.[O:34]=[C:35]1[CH2:39][CH2:38][CH2:37][N:36]1[CH2:40][CH2:41][CH2:42][NH2:43]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([NH:43][CH2:42][CH2:41][CH2:40][N:36]1[CH2:37][CH2:38][CH2:39][C:35]1=[O:34])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 101987Benzyloxycarbonyl-L-proline

생성물 1

HCID 18601121(S)-1-benzyloxycarbonyl-N-[3-(2-oxo-pyrrolidinyl)propyl]-2-pyrrolidine carboxamide수율 29.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In 100 ml of THF was dissolved 9.97 g of compound (29) and after adding slowly thereto 4.45 g of triethylamine and then 6.01 g of isobutyl chloroformate under ice-cooling, the reaction was performed under ice-cooling. To the reaction mixture was slowly added 11.37 g of 3-(2-oxo-1-pyrrolidinyl)-propylamine and then the reaction was performed for one hour under ice-cooling. Precipitates were filtered off, the filtrate was concentrated, and the residue thus formed was subjected to silica gel column chromatography. By eluting the product with ethyl acetatemethanol (4:1), 4.43 g of (S)-1-benzyloxycarbonyl-N-[3-(2-oxo-pyrrolidinyl)propyl]-2-pyrrolidine carboxamide (99) was obtained.

후처리

  1. additionafter adding slowly
  2. temperaturecooling
  3. temperaturecooling
  4. customPrecipitates
  5. filtrationwere filtered off
  6. concentrationthe filtrate was concentrated
  7. customthe residue thus formed
  8. washBy eluting the product with ethyl acetatemethanol (4:1)

출처 및 근거

ORD 기록
ord-c7f8efba479f491d855bc32b4e942921
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04610821

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