1,2-Dichloroethane → (2R)-1-Benzyl-N-(3-hydroxy-4-oxo-1-phenyl-4-(pyridin-2-ylmethylamino)-butan-2-yl)-5-oxopyrrolidine-2-carboxamide

HRID 882843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882843
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@@H:9]1[C:14]([NH:16][CH:17]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:18]([OH:22])[C:19](O)=[O:20])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][NH2:37].O.ON1C2C=CC=CC=2N=N1.C(Cl)CCl.C(N(CC)CC)C>ClCCl>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@@H:9]1[C:14]([NH:16][CH:17]([CH:18]([OH:22])[C:19](=[O:20])[NH:37][CH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=1)[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 666445723-((R)-1-Benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenylbutanoic Acid

Produkt 1

HCID 67095315(2R)-1-Benzyl-N-(3-hydroxy-4-oxo-1-phenyl-4-(pyridin-2-ylmethylamino)-butan-2-yl)-5-oxopyrrolidine-2-carboxamideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

3-((R)-1-benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenylbutanoic acid (300 mg, 0.757 mmol) and pyridin-2-ylmethanamine (94 μl, 98 mg, 0.908 mmol) were dissolved in 13 ml dichloromethane and cooled to 5° C. At this temperature 1-hydroxybenzotriazole hydrate (127 mg, 0.832 mmol), EDC (160 mg, 0.832 mmol) and triethylamine (1.58 ml, 127 mg, 1135 mmol) were successively added. After stirring overnight at room temperature the reaction mixture was concentrated under reduced pressure, water was added and the mixture extracted three times with ethyl acetate. The combined organic layers were successively washed with aq. saturated NaHCO3 solution and brine, dried over Na2SO4 and the solvent was removed under reduced pressure. Column chromatography on silica gel using dichloromethane/MeOH (97/3), followed by dichloromethane/MeOH (95/5), resulted in the title compound (125 mg, yield: 34%) as a white powder.

Aufarbeitung

  1. concentrationwas concentrated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture extracted three times with ethyl acetate
  4. washThe combined organic layers were successively washed with aq. saturated NaHCO3 solution and brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e33cfa8c73684671bd31e07362352c90
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236798B2

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