Thymine → (2R,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-(thymin-1-yl)-2,5-dihydrofuran

HRID 1503307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503307
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].[C:10]([O:14][C:15]([O:17][CH2:18][C@@:19]1([C:32]#[CH:33])[O:23][C@@H:22](OC(OC(C)(C)C)=O)[CH:21]=[CH:20]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CN(C=O)C.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:10]([O:14][C:15]([O:17][CH2:18][C@@:19]1([C:32]#[CH:33])[O:23][C@@H:22]([N:1]2[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]2=[O:3])[CH:21]=[CH:20]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Komponenten

5

Edukt 2

HCID 1135ThymineHCID 53372554(2S,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-t-butoxycarbonyloxy-2,5-dihydrofuran

Produkt 1

HCID 53372555(2R,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-(thymin-1-yl)-2,5-dihydrofuranAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Thymine (16.7 g), N,N′-dimethylformamide (162 g), and tetrakis(triphenylphosphine)palladium(0) (917 mg) were added to a glass reactor under nitrogen, and the mixture was heated to 55° C. Then, a solution of (2S,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-t-butoxycarbonyloxy-2,5-dihydrofuran (β/α=>99/1) (9.0 g) in N,N′-dimethylformamide was added dropwise thereto, and the mixture was stirred for 30 minutes. The reaction mixture was filtered, and water was added to the filtrate, followed by stirring for phase separation. The thus-separated organic layer was concentrated. The residue was purified through recrystallization from acetonitrile and toluene, to thereby yield 6.5 g of (2R,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-(thymin-1-yl)-2,5-dihydrofuran (yield: 72%, β/α=>99/1). The 1H-NMR data of the compound are as follows.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. additionwater was added to the filtrate
  3. stirringby stirring for phase separation
  4. concentrationThe thus-separated organic layer was concentrated
  5. customThe residue was purified through recrystallization from acetonitrile and toluene

Quellen und Nachweise

ORD-Eintrag
ord-df253cb17a4d492dbb6df74ec33400d0
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212174B2

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