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

HRID 64840

Reaktionsgleichung

Reaktionsgleichung von HRID 64840
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 18601121(S)-1-benzyloxycarbonyl-N-[3-(2-oxo-pyrrolidinyl)propyl]-2-pyrrolidine carboxamideAusbeute 29,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c7f8efba479f491d855bc32b4e942921
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04610821

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