1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 19810407, Verbindung

HRID 373497

Reaktionsgleichung

Reaktionsgleichung von HRID 373497
Cl.CN(C)CCCN=C=NCC.[C:13]([O:17][C:18]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH3:29][CH:30]([S:32]([NH2:35])(=[O:34])=[O:33])[CH3:31]>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[CH:30]([S:32]([NH:35][C:24]([C:23]1[CH:22]=[CH:21][C:20]([C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])=[CH:28][CH:27]=1)=[O:26])(=[O:34])=[O:33])([CH3:31])[CH3:29]

Komponenten

7

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27609544-(tert-Butoxycarbonyl)benzoic acidHCID 3549191Propane-2-sulfonamide

Produkt 1

HCID 19810407HCID 19810407, VerbindungAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (198 mg) was added to a stirred mixture of 4-(t-butoxycarbonyl)benzoic acid (195 mg), 2-propanesulfonamide (98 mg) and 4-dimethylaminopyridine (126 mg) in dichloromethane (3.7 ml). The mixture was stirred overnight, diluted with ethyl acetate, washed (1N HCl, brine), dried (MgSO4), and evaporated. The crude product was purified by flash chromatography, eluting with acetone:hexanes (75:25), to afford the product (193 mg): TLC, Rf =0.64, acetone:hexanes (75:25): MS, m/e=356(M+29), 330(M+3), 329(M+2), 328(M+1), 272, 223, 222, 205, 204, 166.

Aufarbeitung

  1. washwashed (1N HCl, brine)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe crude product was purified by flash chromatography
  5. washeluting with acetone:hexanes (75:25)

Quellen und Nachweise

ORD-Eintrag
ord-399b20e674fb4381b5e6e750f26db590
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05164371

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