Methanesulfonic acid, aminoimino- → HCID 178512793, Verbindung

HRID 865340

Reaktionsgleichung

Reaktionsgleichung von HRID 865340
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([CH2:11][CH2:12][N:13]1[CH2:19][CH2:18][CH2:17][C:16]2[CH:20]=[CH:21][C:22]([C:24]#[C:25][CH2:26][CH2:27][CH2:28][NH2:29])=[CH:23][C:15]=2[C:14]1=[O:30])([OH:10])=[O:9].[C:31](S(O)(=O)=O)([NH2:33])=[NH:32]>C(O)(=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([CH2:11][CH2:12][N:13]1[CH2:19][CH2:18][CH2:17][C:16]2[CH:20]=[CH:21][C:22]([C:24]#[C:25][CH2:26][CH2:27][CH2:28][NH:29][C:31]([NH2:33])=[NH:32])=[CH:23][C:15]=2[C:14]1=[O:30])([OH:10])=[O:9]

Komponenten

4

Edukt 2

HCID 9877361Methanesulfonic acid, aminoimino-HCID 22905359HCID 22905359, Verbindung

Produkt 1

HCID 178512793HCID 178512793, VerbindungAusbeute 15,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 2-(2-carboxyethyl)-8-(5-aminopentynyl)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one trifluoroacetate (20 mg, 0.063 mmol) in saturated aqueous KHCO3 (1 mL) was treated with formamidine sulfonic acid (80 mg, 1.0 mmol), and the resulting mixture stirred for 2 hours. The mixture was then treated with acetic acid, and the volatiles were removed. The residue was purified by HPLC (1/2" C-18 reverse-phase column) eluting with a gradient of 3:7 methanol (0.1% trifluoroaceate)/water (0.1% trifluoroaceate), time 0 to 10 min, to 7:3 methanol (0.1% trifluoroaceate)/water (0.1% trifluoroaceate), time 10 to 40 min, to yield 4.5 mg (15%) of 2-(2-carboxyethyl)-8-(5-guanidinopentynyl)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one trifluoroacetate as a light brown solid; 1H NMR(D2O) d7.40(s, 1H), 7.25(dd, J=3, 6 Hz, 1H), 7.15(d, J=6 Hz, 1H), 3.80(t, J=6 Hz, 2H), 3.30(m, 4H), 3.15(t, J=6 Hz, 2H), 2.00(t, J=6 Hz, 2H), 1.80(m, 2H); MS(FAB) m/z=357.1(MH+).

Aufarbeitung

  1. customthe volatiles were removed
  2. customThe residue was purified by HPLC (1/2" C-18 reverse-phase column)
  3. washeluting with a gradient of 3:7 methanol (0.1% trifluoroaceate)/water (0.1% trifluoroaceate), time 0 to 10 min, to 7:3 methanol (0.1% trifluoroaceate)/water (0.1% trifluoroaceate), time 10 to 40 min

Quellen und Nachweise

ORD-Eintrag
ord-2c37b5543ed642629c7eb8e10883303c
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565449

Verknüpfte Notizen

Wird geladen…