Potassium Carbonate → (2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-methoxybenzyl)amino]-4-methylpentanoic acid amide

HRID 507292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507292
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([NH2:15])=[O:14])[CH2:32][C:31]2[CH:34]=[CH:35][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 59001058(2R)-2-(4-Chlorobenzenesulfonylamino)-4-methylpentanoic acid amide

Produkt 1

HCID 9867067(2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-methoxybenzyl)amino]-4-methylpentanoic acid amideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(2R)-2-(4-Chlorobenzenesulfonylamino)-4-methylpentanoic acid amide (300 mg, 1 mmol), K2CO3 (170 mg, 1.2 mmol), and 4-methoxybenzyl chloride (170 mg, 1.1 mmol) in DMF (25 mL) was heated to 60° C. for 18 h. The reaction was then diluted with EtOAc (150 mL) and washed with H2O, brine, dried over MgSO4 and concentrated to give a crude white wax. Further purification by flash chromatography (SiO2, 25% EtOAc/hexanes) afforded the titled compound (297 mg) as a white solid in 70% yield. [α]D=+44.2 (c 1.00, MeOH); MS (ESI), (M−H)− 422.9; 1H NMR (CDCl3) δ 7.63 (d, 2H, J=7.0), 7.42 (d, 2H, J=7.0), 7.25 (d, 2H, J=8.0), 6.79 (d, 2H, J=8.0), 6.25 (br s, 1H), 5.35 (br s, 1H), 4.36 (dd, 2H, J=50, 15), 4-26 (t, 1H, J=7.2), 3.78 (s, 3H), 1.83 (m, 1H), 1.18-1.34 (m, 2H), 0.75 (d, 3H, J=7.0), 0.67 (d, 3H, J=7.0); IR (KBr) 3480, 2959, 1693, 1674, 1514, 1333, 1158 cm−1.

Aufarbeitung

  1. washwashed with H2O, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto give a crude white wax
  5. customFurther purification by flash chromatography (SiO2, 25% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fb240e896cc6475fac058c58c89c2da3
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786122B2

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