Dimethylformamide → (R)-3-(4-propoxybenzamido)-4-(trimethylammonio)butanoate

HRID 1958703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1958703
[CH3:1][N+:2]([CH2:5][C@H:6]([NH2:11])[CH2:7][C:8]([O-:10])=[O:9])([CH3:4])[CH3:3].[CH2:12]([O:15][C:16]1[CH:31]=[CH:30][C:19]([C:20](ON2C(=O)CCC2=O)=[O:21])=[CH:18][CH:17]=1)[CH2:13][CH3:14].CN(C=O)C.C(N(C(C)C)CC)(C)C>C(OCC)C>[CH2:12]([O:15][C:16]1[CH:31]=[CH:30][C:19]([C:20]([NH:11][C@@H:6]([CH2:5][N+:2]([CH3:3])([CH3:4])[CH3:1])[CH2:7][C:8]([O-:10])=[O:9])=[O:21])=[CH:18][CH:17]=1)[CH2:13][CH3:14]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 121830EmeriamineHCID 866412122,5-Dioxopyrrolidin-1-yl 4-propoxybenzoate

Produkt 1

HCID 25065699(R)-3-(4-propoxybenzamido)-4-(trimethylammonio)butanoateAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

(R)-aminocarnitine (20 mg, 0.12 mmol) and 2,5-dioxopyrrolidin-1-yl 4-propoxybenzoate (42 mg, 0.15 mmol) were dissolved into DMF (0.5 mL). Diisopropylethylamine (63 μL, 0.36 mmol) was added and the solution was stirred at room temperature for 18 h. Diethyl ether (20 mL) was added and a white precipitate was collected. The white solid was triturated with 1:1 acetone/ether and dried to give the title compound as a white powder (8.1 mg, 21%). 1H NMR (300 MHz, CD3OD) δ 7.89-7.78 (m, 2H), 7.01 (d, 2H, J=7.8 Hz), 4.75-4.63 (m, 1H), 4.02 (t, 2H, J=7.2 Hz), 3.75-3.51 (m, 2H), 3.21 (s, 9H), 2.82-2.71 (m, 2H), 1.85-1.75 (m, 2H), 1.05 (t, 3H, J=7.0 Hz); MS ESI 323.1 [M+H]+, calcd for [C17H26N2O4+H]+ 323.19.

Aufarbeitung

  1. customa white precipitate was collected
  2. customThe white solid was triturated with 1:1 acetone/ether
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4ef705310fd2495292be8cb121fc174f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410150B2

Notizen zur Reaktion

Wird geladen…