1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-Chloro-phenyl)-3-methoxy-N-[2-oxo-2-(2-phenyl-pyrrolidin-1-yl)-ethyl]-benzene sulfonamide

HRID 2079606

Reaktionsgleichung

Reaktionsgleichung von HRID 2079606
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:20][C:21](O)=[O:22])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:54]1([CH:60]2[CH2:64][CH2:63][CH2:62][NH:61]2)[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:20][C:21](=[O:22])[N:61]2[CH2:62][CH2:63][CH2:64][CH:60]2[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)(=[O:10])=[O:11])=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2618922-PhenylpyrrolidineHCID 57788180[(4-Chlorophenyl)-(3-methoxy-benzenesulfonyl)-amino]-acetic acid

Produkt 1

HCID 44197669N-(4-Chloro-phenyl)-3-methoxy-N-[2-oxo-2-(2-phenyl-pyrrolidin-1-yl)-ethyl]-benzene sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of [(4-chlorophenyl)-(3-methoxy-benzenesulfonyl)-amino]-acetic acid (250 mg, 0.7 mmol) in dry dichloromethane (20 mL) were sequentially added EDCI (202 mg, 1.05 mmol), HOBT (142.4 mg, 1.05 mmol), and DIPEA (0.23 mL, 1.40 mmol). The reaction mixture was allowed to stir for 30 minutes under nitrogen at 25° C. 2-Phenyl-pyrrolidine (104 mg, 0.7 mmol) was added and the mixture was stirred at 25° C. for 12 h. The reaction mixture was diluted with dichloromethane (20 mL), washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution and water. The organic layer was dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography over silica gel (30-40% ethyl acetate/hexane) to yield the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at 25° C. for 12 h
  2. washwashed with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel (30-40% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-45eec1ad653542c1b3d0b342572f17f0
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932269B2

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