EDTA disodium salt → {(3aR,4R,6R,6aR)-6-[6-(4-Fluorobenzyl)-9H-purin-9-yl]-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}methyl acetate

HRID 552717

Reaktionsgleichung

Reaktionsgleichung von HRID 552717
[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:13]2[C@@H:9]([O:10][C:11]([CH3:15])([CH3:14])[O:12]2)[C@H:8]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3Cl)[O:7]1)(=[O:3])[CH3:2].[Cl-].[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][Zn+])=[CH:30][CH:29]=1.[NH4+].[Cl-].C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=O.[Na+].[Na+]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:13]2[C@@H:9]([O:10][C:11]([CH3:15])([CH3:14])[O:12]2)[C@H:8]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[CH2:32][C:31]2[CH:34]=[CH:35][C:28]([F:27])=[CH:29][CH:30]=2)[O:7]1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 8759EDTA disodium saltHCID 25517Ammonium ChlorideHCID 86607315((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl acetateHCID 178505764HCID 178505764, Verbindung

Produkt 1

HCID 67164294{(3aR,4R,6R,6aR)-6-[6-(4-Fluorobenzyl)-9H-purin-9-yl]-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}methyl acetateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

[(3aR,4R,6R,6aR)-6-(6-Chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl acetate (369 mg, 0.00100 mol) and tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.000050 mol) were dissolved in tetrahydrofuran (10 mL) at room temperature under nitrogen. 0.5 M of 4-fluorobenzylzinc chloride in tetrahydrofuran (3 mL) was added dropwise over 10 min. The solution was stirred under nitrogen at room temperature for 15 min then heated at 60° C. for 3 h. The reaction was allowed to cool to r.t then poured on saturated NH4Cl (10 mL). Saturated Na2EDTA (10 mL) was added and the solution extracted three times with EtOAc. The organics were pooled and extracted twice with saturated Na2EDTA then once with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (DCM/EtOAc 10% to 50%) to obtain the product (322 mg, 73%) as an oil.

Aufarbeitung

  1. temperaturethen heated at 60° C. for 3 h
  2. temperatureto cool
  3. extractionthe solution extracted three times with EtOAc
  4. extractionextracted twice with saturated Na2EDTA
  5. dry with materialonce with brine, dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (DCM/EtOAc 10% to 50%)

Quellen und Nachweise

ORD-Eintrag
ord-602aae8bd26141b699a258d8e039412d
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951810B2

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