Triethylamine → tert-Butyl (3-(methoxyimino)-3-(4-methoxyphenyl)-propanamido)(methylthio)methylenecarbamate

HRID 133790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133790
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[CH2:5][C:6]([OH:8])=O.[NH2:17][C:18](=[N:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[S:19][CH3:20].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[CH2:5][C:6]([NH:17][C:18](=[N:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[S:19][CH3:20])=[O:8]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54237411CarbaMic acid, [iMino(Methylthio)Methyl]-, 1,1-diMethylethyl ester (9CI)HCID 589845323-(Methoxyimino)-3-(4-methoxyphenyl)propanoic acid

Produkt 1

HCID 72481141tert-Butyl (3-(methoxyimino)-3-(4-methoxyphenyl)-propanamido)(methylthio)methylenecarbamateAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-(methoxyimino)-3-(4-methoxyphenyl)propanoic acid (223 mg), tert-butyl amino(methylthio)methylenecarbamate (190 mg), EDAC.HCl (384 mg), DMAP (122 mg) and triethylamine (0.56 mL) in dichloromethane (3 mL) was stirred at room temperature for 12 h. The crude reaction mixture was purified directly by preparative TLC eluting with 35% ethyl acetate/75% hexanes to give the title compound as a yellowish oil (350 mg). HPLC retention time: 2.42 min (method A). MS (ESI) (M+Na)+ 418.18.

Aufarbeitung

  1. customThe crude reaction mixture
  2. customwas purified directly by preparative TLC
  3. washeluting with 35% ethyl acetate/75% hexanes

Quellen und Nachweise

ORD-Eintrag
ord-82c15c6d766446c481efedaa853fc77c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390925B2

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