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Hydrochloric Acid → HCID 57200673, Verbindung

HRID 374555
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 374555
[Cl:1][C:2]1[C:3]([N:20]2[CH2:28][C@@H:27]3[C@@H:22]([CH2:23][CH2:24][CH2:25][NH:26]3)[CH2:21]2)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].C[Si](NC(=O)C(F)(F)F)(C)C.Cl[CH2:41][C:42]1[CH2:49][S:48][C@H:47]2[N:44]([C:45](=[O:60])[C@H:46]2[NH:50][C:51](=[O:59])[CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:43]=1[C:61]([O:63][CH:64]([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[O:62].[Na+].[I-].Cl>ClCCl.CC(C)=O.O>[CH:64]([O:63][C:61]([C:43]1[N:44]2[C@H:47]([S:48][CH2:49][C:42]=1[CH2:41][N:26]1[CH2:25][CH2:24][CH2:23][C@@H:22]3[C@H:27]1[CH2:28][N:20]([C:3]1[C:2]([Cl:1])=[C:11]4[C:6]([C:7](=[O:18])[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]4[CH:12]4[CH2:14][CH2:13]4)=[CH:5][C:4]=1[F:19])[CH2:21]3)[C@H:46]([NH:50][C:51](=[O:59])[CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)[C:45]2=[O:60])=[O:62])([C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 119375BAY-Y-3118 free baseHCID 555527Acetamide, 2,2,2-trifluoro-N-(trimethylsilyl)-HCID 11145881HCID 11145881, Verbindung

Produkt 1

HCID 57200673
HCID 57200673, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under an N2 atmosphere, 160 mg (0.4 mmol) of 8-chloro-1-cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]non-8-yl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are suspended in 2.25 ml of dichloromethane. 283 μl (1.6 mmol) of trimethylsilyltrifluoroacetamide are added and the mixture is stirred at room temperature for 20 minutes; 0.5 g of 3 Å molecular sieves is then added, and the mixture is stirred at room temperature for one hour, and the solution is evaporated to dryness. Subsequently, a solution of 151 mg (0.283 mmol) of benzhydryl [6R,7R]-3-chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate in 2.25 ml of acetone is added. After addition of 46.6 mg (0.367 mmol) of NaI, the mixture is stirred overnight (20 hours), poured into water, adjusted to pH=4 with 1N HCl, and extracted 3× with ethyl acetate. The organic phase is washed with water, dried over MgSO4 and evaporated to dryness. 96 mg (0.106 mmol) (38% of theory) of the title product are obtained by chromatography on silica gel using CH2Cl2 /CH3OH (30:1).

Aufarbeitung

  1. addition0.5 g of 3 Å molecular sieves is then added
  2. stirringthe mixture is stirred at room temperature for one hour
  3. customthe solution is evaporated to dryness
  4. stirringthe mixture is stirred overnight (20 hours)
  5. extractionextracted 3× with ethyl acetate
  6. washThe organic phase is washed with water
  7. dry with materialdried over MgSO4
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ef11097c9c1840be84b562303c9d5969
Quelldatensatz
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05480879

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