Ethyl 4,6-diiodo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate → 3-(2-carboxyethyl)-4,6-diiodo-1H-indole-2-carboxylic acid

HRID 467426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467426
[I:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[C:7]2[C:3]=1[C:4]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[C:5]([C:12]([O:14]CC)=[O:13])[NH:6]2.O.O.O.[OH-].[Li+]>O1CCCC1.O>[C:19]([CH2:18][CH2:17][C:4]1[C:3]2[C:7](=[CH:8][C:9]([I:11])=[CH:10][C:2]=2[I:1])[NH:6][C:5]=1[C:12]([OH:14])=[O:13])([OH:21])=[O:20]

Komponenten

5

Edukt 2

HCID 71281158Ethyl 4,6-diiodo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylateHCID 86677587Lithium hydroxide trihydrate

Produkt 1

HCID 712809393-(2-carboxyethyl)-4,6-diiodo-1H-indole-2-carboxylic acidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Ethyl 4,6-diiodo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate (1.71 g, 5 mmol) was dissolved in 15 ml tetrahydrofurane (THF) with stirring at rt. Then a solution of 0.63 g of lithium hydroxide trihydrate (3 equiv.) in 15 ml water was added and the resulting mixture was let to stir at rt for 24 h. After completion of the reaction THF was removed under reduced pressure and the pH was adjusted to 4-5, and the product was extracted with diethyl ether (3×15 ml). The organic layers were dried over magnesium sulfate, filtered, and evaporated to dryness to yield a light-beige-colored solid in 95-100% yield. mp. 280-282° C. 1H-NMR (DMSO-d6) δ 2.48 (m, 2H, 2′-H); 3.49 (m, 2H, 1′-H); 7.78 (dd, 2H, J=1.7 Hz, 5-H, 7-H); 11.80 (s, 1H, NH); 12.68 (b, 2H, 2CO2H). 13C-NMR (DMSO-d6) δ 18.9 (C-2′); 36.4 (C-1′), 88.3 (C-4); 89.5 (C-6); 121.4 (C-7); 122.0 (C-3); 126.2 (C-2); 126.4 (C-3a); 137.8 (C-7a); 138.1 (C7); 162.7 (2′-CO2H); 173.58 (2-CO2H). LC-MS (m/z): 503 [M+NH4+]+, 486 [M]+, 484 [M]−. Purity (LC-MS): 98%.

Aufarbeitung

  1. stirringto stir at rt for 24 h
  2. customwas removed under reduced pressure
  3. extractionthe product was extracted with diethyl ether (3×15 ml)
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto yield a light-beige-colored solid in 95-100% yield

Quellen und Nachweise

ORD-Eintrag
ord-069781a446f44796a2d5b0cd785e7909
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623593B1

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