Methanesulfonic acid, aminoimino- → HCID 178481554, Verbindung

HRID 1488665

Reaktionsgleichung

Reaktionsgleichung von HRID 1488665
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][N:9]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:19][C:14]=2[C:13](=[O:26])[N:12]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:11][C:10]1=[O:32].[C:33](S(O)(=O)=O)([NH2:35])=[NH:34]>C(=O)(O)[O-].[K+]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][N:9]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH:25][C:33]([NH2:35])=[NH:34])=[CH:19][C:14]=2[C:13](=[O:26])[N:12]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:11][C:10]1=[O:32]

Komponenten

4

Edukt 2

HCID 9877361Methanesulfonic acid, aminoimino-HCID 229051171-methyl-4-(2-carboxyethyl)-7-(5-amino-1-pentynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione trifluoracetate

Produkt 1

HCID 178481554HCID 178481554, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516893Potassium BicarbonateLösungsmittel

Versuchsvorschrift

To a magnetically stirred solution of 6 mgs of 1-methyl-4-(2-carboxyethyl)-7-(5-amino-1-pentynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione trifluoracetate (0.017 mol) in 1.0 mL 10% potassium bicarbonate was added 31.0 mgs of formamidine sulfonic acid (0.25 mmol). After 30 minutes, the reaction mixture was quenched with 0.5 mL acetic acid and concentrated in vacuo. The resulting residue was diluted with 2 mL water and purified by high pressure liquid chromatography, using a 1/2" C-18 reverse-phase column, eluting with a solvent gradient of 10:90 methanol (0.1% trifluoracetic acid)/water (0.1% trifluoracetic acid), time 0 to 10 min, to 50:50 methanol (0.1% trifluoracetic acid)/water (0.1% trifluoracetic acid), time 10 min to 40 min, flow=10 ml/min (Rt =36.8 min, un detection 254 nm) to yield 4.5 mgs (67%) 1-methyl-4-(2-carboxyethyl)-7-(5-guandino-1-pentynyl)-3,4-dihydro-1H-1, 4-benzodiazepine-2,5-dione trifluoracetate. HRMS (FAB) molecular ion m/z=386.1823 (cald. C19H24N5O4, 386.1829). 1H NMR (D2O) 7.60 (1H,d,4JHH, Ar-H o-CON), 7.51 (1H,dd, 4 JHH=2 Hz, 3JHH=8 Hz, Ar-H p-CON), 7.20 (1H,d,3JHH=8 Hz, ArH m-CON), 4.05 (1H,d, 2JHH=14 Hz, NCHHCO), 3.92 (1H,m,NCHHCH2), 3.72 (1H,d,2JHH=14 Hz, NCHHCO), 3.40 (1H,m,NCHHCH2), 3.23-3.15 (5H,NCH3H2NC(=NH2)NHCH2), 2.58 (2H,m, CH2 CO2), 2.38 (2H,t,3JHH=7 Hz, CjCCH2), 1.76 (2H,p,3 JHH=7 Hz, CH2CH2CH2).

Aufarbeitung

  1. customthe reaction mixture was quenched with 0.5 mL acetic acid
  2. concentrationconcentrated in vacuo
  3. additionThe resulting residue was diluted with 2 mL water
  4. custompurified by high pressure liquid chromatography
  5. washeluting with a solvent gradient of 10:90 methanol (0.1% trifluoracetic acid)/water (0.1% trifluoracetic acid), time 0 to 10 min, to 50:50 methanol (0.1% trifluoracetic acid)/water (0.1% trifluoracetic acid), time 10 min to 40 min, flow=10 ml/min (Rt =36.8 min, un detection 254 nm)

Quellen und Nachweise

ORD-Eintrag
ord-9aaa5b28c9b84d0da771e6540c888e29
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05674865

Verknüpfte Notizen

Wird geladen…