Chlorotrimethylsilane → HCID 135903213, Verbindung
Reaktionsgleichung
[NH2:1][C:2]1[NH:3][C:4](=[O:32])[C:5]2[N:6]=[CH:7][N:8]([C@@H:11]3[O:15][C@H:14]([CH2:16][CH:17]([P:26](=[O:29])([OH:28])[OH:27])S(C4C=CC=CC=4)=O)[C@@H:13]([F:30])[C@H:12]3[OH:31])[C:9]=2[N:10]=1.C(N(CCCC)CCCC)CCC.C[Si](Cl)(C)C>CN(C=O)C>[NH2:1][C:2]1[NH:3][C:4](=[O:32])[C:5]2[N:6]=[CH:7][N:8]([C@@H:11]3[O:15][C@H:14](/[CH:16]=[CH:17]/[P:26](=[O:27])([OH:29])[OH:28])[C@@H:13]([F:30])[C@H:12]3[OH:31])[C:9]=2[N:10]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 130 °C
Versuchsvorschrift
Compound 35.18 (12 mg, 0.025 mmol) was dissolved in anhydrous DMF (4 mL), treated with tributylamine (0.12 mL, 0.5 mmol) and TMSCl (0.063 mL, 0.5 mmol). The mixture was heated to 130° C. for 4 h, cooled to r.t., and then quenched with 2 mL water. The mixture was stirred at r.t for another 2 h and then the solvent was removed under reduced pressure. The residue was washed with 3×20 mL acetonitrile to remove TBA and TMSOH. The acetonitrile washes were discarded and the solid was dissolved in water, subjected to a reverse phase HPLC to give compound 35.19 (6.6 mg, 73% yield). 1HNMR (D2O, 300 MHz) δ 8.40 (s, 1H), 6.57 (m, 1H), 6.13 (t, 1H), 5.92 (d, 1H), 4.90-5.20(m, 3H). 31PNMR (D2O, 300 MHz): 11.815 ppm. LRMS (ESI) MH+ C11H13FN5O6P requires 362.1. Found 362.0.
Aufarbeitung
- temperaturecooled to r.t.
- customquenched with 2 mL water
- customthe solvent was removed under reduced pressure
- washThe residue was washed with 3×20 mL acetonitrile
- customto remove TBA and TMSOH
- dissolutionthe solid was dissolved in water
Quellen und Nachweise
- ORD-Eintrag
- ord-3637144873a04897a10bd924a1183a68
- Quelldatensatz
- uspto-grants-2012_12
- Patentnummer
- US08324179B2
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