Acetic Acid → HCID 72427427, Verbindung

HRID 346937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 346937
[C:1]([O:5][C:6](=[O:52])[NH:7][CH:8]1[C:26](=[O:27])[N:25]2[CH:21]([CH2:22][CH:23]([O:28][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][N:30]=3)[CH2:24]2)[C:20](=[O:39])[NH:19][C:18]2([C:40]([NH:42][S:43]([C:46]3([CH2:49][CH2:50][CH3:51])[CH2:48][CH2:47]3)(=[O:45])=[O:44])=[O:41])[CH:16]([CH2:17]2)[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].N(C([O-])=O)=NC([O-])=O.[K+].[K+].C(O)(=O)C>CO>[C:1]([O:5][C:6](=[O:52])[NH:7][CH:8]1[C:26](=[O:27])[N:25]2[CH:21]([CH2:22][CH:23]([O:28][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][N:30]=3)[CH2:24]2)[C:20](=[O:39])[NH:19][C:18]2([C:40]([NH:42][S:43]([C:46]3([CH2:49][CH2:50][CH3:51])[CH2:47][CH2:48]3)(=[O:44])=[O:45])=[O:41])[CH:16]([CH2:17]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 176Acetic Acid2×HCID 6096233Potassium diazene-1,2-dicarboxylate2×HCID 68751392[18-(Isoquinolin-1-yloxy)-2,15-dioxo-4-(1-propyl-cyclopropanesulfonylaminocarbonyl)-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester

Produkt 1

HCID 72427427HCID 72427427, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a mixture of 73 mg (0.1 mmol) of [18-(Isoquinolin-1-yloxy)-2,15-dioxo-4-(1-propylcyclopropanesulfonylamino-carbonyl)-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester in 3 mL of methanol was added 332 mg (2 mmol)of dipotassium azodicarboxylate. Glacial acetic acid (240 mg, 4 mmol) in 2 mL of methanol was added slowly by a syringe pump over 5 h. The mixture was stirred at rt. After 5 h, another 332 mg (2 mmol) of dipotassium azodicarboxylate and 240 mg (4 mmol) of glacial acetic acid was added over the course of 5 h and the stirring was continued overnight. This cycle was repeated twice. LC-MS showed about 40% starting material still remaining. The solvent was then removed on a rotary evaporator. Water was added to the residue and the mixture was extracted three times with ethyl acetate. It was then dried with magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was dissolved in methanol and purified by preparative HPLC (YMC ODS-A, S5, 20×100 mm, gradient: 80% B to 85% B, 15 min, hold 2 min, flow rate 25 mL/min) to isolate the product as a white powder (25 mg, 34%).

Aufarbeitung

  1. waitthe stirring was continued overnight
  2. customThe solvent was then removed on a rotary evaporator
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. dry with materialIt was then dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting oil was dissolved in methanol
  9. custompurified by preparative HPLC (YMC ODS-A, S5, 20×100 mm, gradient: 80% B to 85% B, 15 min, hold 2 min, flow rate 25 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-403ed41133ee497b9d2109c086706b9b
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173004B2

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