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Trimethylsilyl triflate → Methyl 9-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-ethyl-2H-tetraazol-5-yl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate

HRID 1168301
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1168301
[C:1]1([CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29]([O:32][C@H:33]1[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[CH:36](OC(=O)C)[O:35][C@@H:34]1[C:46]1[N:47]=[N:48][N:49]([CH2:51][CH3:52])[N:50]=1)(=[O:31])[CH3:30].C[Si](OS(C(F)(F)F)(=O)=O)(C)C>ClC(Cl)(Cl)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:39]([O:38][C@@H:37]1[C@H:33]([O:32][C:29](=[O:31])[CH3:30])[C@@H:34]([C:46]2[N:47]=[N:48][N:49]([CH2:51][CH3:52])[N:50]=2)[O:35][C@H:36]1[N:14]1[CH:13]=[N:12][C:11]2[C:15]1=[N:16][C:17]([C:19]([O:21][CH3:22])=[O:20])=[N:18][C:10]=2[NH:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:41])[CH3:40]
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Komponenten

7

Edukt 3

HCID 65367Trimethylsilyl triflateHCID 11302289(2R,3R,4R)-4,5-bis(acetoxy)-2-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetateHCID 178418823HCID 178418823, Verbindung

Produkt 1

HCID 59094502Methyl 9-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-ethyl-2H-tetraazol-5-yl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylateAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 1140TolueneLösungsmittelHCID 62781,1,1-TrichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of methyl 6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 29) (0.4 g, 1.07 mmol) in 1,1,1-trichloroethane (25 ml) was treated with N,O-bis(trimethylsilylacetamide) (1.6 ml, 6.54 mmol) and the mixture was heated under reflux for one hour. The solvent was removed under reduced pressure and the residue was twice azeotroped with toluene. The residue was dissolved in toluene (5 ml) and treated sequentially with a solution of (2R,3R,4R)-4,5-bis(acetyloxy)-2-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetate (WO-A-9967265) (0.45 g, 1.31 mmol) in toluene (20 ml) and then trimethylsilyltriflate (0.25 ml, 1.37 mmol). The mixture was heated under reflux for 3 hours and then allowed to stand at room temperature overnight. The solution was diluted with ethyl acetate (40 ml), washed sequentially with saturated aqueous sodium hydrogen carbonate solution (20 ml) and brine (20 ml), dried (anhydrous magnesium sulphate) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:ethyl acetate (80:20 by volume) gradually changing to dichloromethane:ethyl acetate (60:40 by volume) to afford the title compound (0.44 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was twice azeotroped with toluene
  5. dissolutionThe residue was dissolved in toluene (5 ml)
  6. temperatureThe mixture was heated
  7. temperatureunder reflux for 3 hours
  8. washwashed sequentially with saturated aqueous sodium hydrogen carbonate solution (20 ml) and brine (20 ml)
  9. dry with materialdried (anhydrous magnesium sulphate)
  10. customevaporated under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:ethyl acetate (80:20 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-9b1af8abcfa04879b3666d659fbd159d
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06624158B2

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