Triethylamine → cis-6-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylic acid

HRID 736706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736706
[NH2:1][C@H:2]1[CH2:7][CH:6]=[CH:5][CH2:4][C@H:3]1[C:8]([OH:10])=[O:9].C(N(CC)CC)C.Cl.[CH3:19][C:20]1[CH:29]=[C:28]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1>O1CCOCC1.O>[CH3:19][C:20]1[CH:29]=[C:28]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([S:38]([NH:1][C@@H:2]3[C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH:5]=[CH:6][CH2:7]3)(=[O:40])=[O:39])=[CH:34][CH:33]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2724811cis-2-Amino-4-cyclohexene-1-carboxylic acidHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

Produkt 1

HCID 68819512cis-6-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylic acidAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 423.5 mg (3 mmol) of cis-2-amino-4-cyclohexene-1-carboxylic acid in 8 mL of dioxane and 8 mL of water was added 2.1 mL of triethylamine, followed by 1.13 g (3 mmol) of 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride in one portion as a solid. The solution was stirred at room temperature overnight. After removal of the volatile material, 10 mL of dichloromethane and 10 mL of water were added to the residue. The mixture was adjusted pH to 5 with 1N HCl solution. The solid was collected by filtration, washed with a small volume of water, followed by dichloromethane to provide 1.05 g of cis-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylic acid in 77% yield. MS: 453.1 (M+H)+

Aufarbeitung

  1. customAfter removal of the volatile material, 10 mL of dichloromethane and 10 mL of water
  2. additionwere added to the residue
  3. filtrationThe solid was collected by filtration
  4. washwashed with a small volume of water

Quellen und Nachweise

ORD-Eintrag
ord-0d46003e51014df3803d3a83f145843a
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595327B2

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