1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamide

HRID 1801581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1801581
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[S:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)(=[O:14])=[O:13].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:42][C:43]1[CH:44]=[C:45]([C@H:49]([NH2:51])[CH3:50])[CH:46]=[CH:47][CH:48]=1>CN(C=O)C.CCOC(C)=O.O>[Cl:42][C:43]1[CH:44]=[C:45]([C@H:49]([NH:51][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([S:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)(=[O:14])=[O:13])[CH:5]=2)[CH3:50])[CH:46]=[CH:47][CH:48]=1

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7679134-Methoxy-3-(morpholine-4-sulfonyl)benzoic acidHCID 2507697(R)-1-(3-chlorophenyl)ethanamine

Produkt 1

HCID 26908119(R)-N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamideAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-methoxy-3-(morpholinosulfonyl)benzoic acid 42 (0.824 g, 2.73 mmol) in DMF (6 mL) was added EDCI (0.686 g, 3.58 mmol) and HOBT (0.536 g, 3.50 mmol), the solution was stirred for 30 min and (R)-1-(3-chlorophenyl)ethanamine (0.673 g, 4.32 mmol) was added. The reaction mixture was stirred at room temperature for 16 h and diluted with EtOAc and water. The organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 60% to 100% EtOAc in hexanes) gave (R)—N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamide 43 (1.14 g, 95.0% yield) as a white solid. Mass spectrum: calculated for C20H23ClN2O5S 438.1. found 439.1 (M++1).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. washThe organic phase was washed with water (2×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography on silica gel (eluted with 60% to 100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-39ff14e12779404997a7c0d4e4b2f1c6
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349831B2

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