Chlorotrimethylsilane → HCID 68593660, Verbindung

HRID 2191064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191064
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[O:15][CH:14]([CH2:16][CH:17]([P:26](=[O:29])([OH:28])[OH:27])S(C2C=CC=CC=2)=O)[CH:13]([F:30])[CH:12]1[OH:31].C(N(CCCC)CCCC)CCC.C[Si](Cl)(C)C>CN(C=O)C>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[O:15][CH:14]([CH:16]=[CH:17][P:26](=[O:27])([OH:28])[OH:29])[CH:13]([F:30])[CH:12]1[OH:31]

Komponenten

5

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 7622TributylamineHCID 68593093HCID 68593093, Verbindung

Produkt 1

HCID 68593660HCID 68593660, VerbindungAusbeute 31,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Compound 49.4 (147 mg, 0.31 mmol) was dissolved in anhydrous DMF, treated with tributylamine (1.49 mL, 6.24 mmol) and TMSCl (0.79 mL, 6.24 mmol). The mixture was heated to 130° C. for 4 h and then cooled to rt. The reaction was quenched with water and stirred at rt for another 2 h. The mixture was concentrated under reduced pressure and the residue was washed with acetonitrile. The acetonitrile washes were discarded and the residue was dissolved in water, subjected to a reverse phase HPLC to give compound 49.5 (34 mg, 24% yield). 1H NMR (D2O, 300 MHz): δ 4.91-5.17 (m, 3H), 5.92-5.95 (m, 1H), 6.07-6.59 (m, 2H), 8.37 (s, 1H). 31PNMR: 11.82 ppm. LRMS [M−H]− C11H13FN5O5P requires 344.1. Found 344.1.

Aufarbeitung

  1. temperaturecooled to rt
  2. customThe reaction was quenched with water
  3. concentrationThe mixture was concentrated under reduced pressure
  4. washthe residue was washed with acetonitrile
  5. dissolutionthe residue was dissolved in water

Quellen und Nachweise

ORD-Eintrag
ord-168fe75088b64fe89996c55f9f50244d
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324179B2

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