2-Methylbenzenesulfonamide → HCID 53883197, Verbindung

HRID 2371793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371793
[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[C:17]3[CH2:20][C:21]3[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][C:22]=3[O:30][CH3:31])=[CH:12][CH:11]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[S:39]([NH2:42])(=[O:41])=[O:40].Cl.CN(C)CCCN=C=NCC.O1CCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[C:17]3[CH2:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([NH:42][S:39]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[CH3:32])(=[O:40])=[O:41])=[O:26])=[CH:23][C:22]=3[O:30][CH3:31])=[CH:12][CH:11]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 69242-MethylbenzenesulfonamideHCID 8028TetrahydrofuranHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54439973HCID 54439973, Verbindung

Produkt 1

HCID 53883197HCID 53883197, VerbindungAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 4-[7-(cyclopentylacetamido)naphth-1-ylmethyl]-3-methoxybenzoic acid (375 mg), 2-methylbenzenesulfonamide (231 mg), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (259 mg) in methylene chloride (9 ml) was added 4-dimethylamino pyridine (165 mg); and the mixture was stirred for 24 h. The mixture was added to 60 ml of 1:9 tetrahydrofuran:ethyl acetate: and the organic solution was washed (1N HCl, water, brine), dried (MgSO4), and evaporated. The residue was purified by flash chromatorgraphy, eluting methylene chloride:acetone:methanol (90:8:0, 90:8:1, 90:8:2 successively). The crude product was recrystallized from 2:8 methanol:methylene chloride and petroleum ether to give the title compound as a colorless solid (263 mg, 51%); mp 248.0°-249.0° C.

Aufarbeitung

  1. washethyl acetate: and the organic solution was washed (1N HCl, water, brine)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by flash chromatorgraphy
  5. washeluting methylene chloride:acetone:methanol (90:8:0, 90:8:1, 90:8:2 successively)
  6. customThe crude product was recrystallized from 2:8 methanol

Quellen und Nachweise

ORD-Eintrag
ord-72fe17c78507481783667e4f1410f2b9
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05095038

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