Pinoline → 2-(6-Methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyric acid tert-butyl ester

HRID 992427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992427
[C:1]([O:5][C:6](=[O:16])[CH:7]([CH2:11][S:12](Cl)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]1[CH2:28][NH:29][CH2:30][CH2:31][C:22]2=1.C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6](=[O:16])[CH:7]([CH2:11][S:12]([N:29]1[CH2:30][CH2:31][C:22]2[C:21]3[C:25](=[CH:26][CH:27]=[C:19]([O:18][CH3:17])[CH:20]=3)[NH:24][C:23]=2[CH2:28]1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1868PinolineHCID 8471TriethylamineHCID 212590942-Chlorosulfonylmethyl-3-methyl-butyric acid tert-butyl ester

Produkt 1

HCID 698956642-(6-Methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyric acid tert-butyl esterAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2-chlorosulfonylmethyl-3-methylbutyric acid tert-butyl ester (WO 99/24399) (470mg) in dichioromethane (10 ml) was added to a mixture of 6-methoxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (350 mg) and triethylamine (0.72 ml) in dichloromethane (10 ml) at room temperature under nitrogen. The mixture was stirred for 20 minutes before being evaporated to dryness and the residue chromatographed (SiO2, 1:1 heptane-ethyl acetate) to give the title compound (487 mg, 66%) as a white solid.

Aufarbeitung

  1. custombefore being evaporated to dryness
  2. customthe residue chromatographed (SiO2, 1:1 heptane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-018286e1321e448aa767676fbf6f6461
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06469020B2

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