Methyl iodide → methyl (1S,2R)-1-ethyl-2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate

HRID 736827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736827
[CH2:1]([C@:3]1([C:31]([O:33][CH3:34])=[O:32])[CH2:7][CH2:6][CH2:5][C@H:4]1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([CH3:30])[CH:21]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH3:2].[H-].[Na+].I[CH3:38]>C1COCC1>[CH2:1]([C@:3]1([C:31]([O:33][CH3:34])=[O:32])[CH2:7][CH2:6][CH2:5][C@H:4]1[N:8]([CH3:38])[S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([CH3:30])[CH:21]=2)=[CH:14][CH:13]=1)(=[O:10])=[O:11])[CH3:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86607917HCID 86607917, Verbindung

Produkt 1

HCID 86607918methyl (1S,2R)-1-ethyl-2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 204 mg (0.423 mmol) of methyl (1S,2R)-1-ethyl-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate (Example 56, Step 3) in THF (1.5 mL) was added 60% sodium hydride (22 mg, 0.55 mmol) and the resulting mixture was stirred at room temperature for 1 h. Iodomethane (35 μL, 80 mg 0.56 mmol) was added and the reaction was stirred overnight and then quenched with saturated aqueous ammonium chloride. These steps were repeated twice more, until starting material was consumed, and the residue was purified by column chromatography on silica gel eluting with 50% ethyl acetate/hexanes to give methyl (1S,2R)-l -ethyl-2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate (174 mg, 0.350 mmol, 83%) as a colorless solid. 1H NMR (400 MHz, CHLOROFORM-D) □ ppm 0.85 (t, J=7.33 Hz, 3H) 1.29-1.40 (m, 1H) 1.48-1.60 (m, 4H) 1.78-1.87 (m, 1H) 2.20-2.30 (m, J=7.01, 7.01, 7.01, 7.01 Hz, 2H) 2.57 (s, 3H) 2.75 (s, 3H) 3.71 (s, 3H) 5.55 (s, 2H) 7.11 (ddd, J=9.41, 2.78, 2.46 Hz, 2H) 7.42 (s, 1H) 7.55 (ddd, J=8.27, 6.88, 1.26 Hz, 1H) 7.70-7.76 (m, 3H) 7.90 (d, J=7.58 Hz, 1H) 8.09 (d, J=7.83 Hz, 1H).

Aufarbeitung

  1. stirringthe reaction was stirred overnight
  2. customquenched with saturated aqueous ammonium chloride
  3. customwas consumed
  4. customthe residue was purified by column chromatography on silica gel eluting with 50% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5be19d3859c946b0811403d844677421
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595327B2

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