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2,2-Dimethoxypropane → ((3aR,4R,6R,6aS)-6-(5-Iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol

HRID 1507478
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1507478
[OH:1][CH2:2][C@H:3]1[CH2:7][C@@H:6]([NH:8][C:9]2[C:14]([I:15])=[C:13]([O:16][CH3:17])[N:12]=[C:11]([S:18][CH3:19])[N:10]=2)[C@H:5]([OH:20])[C@@H:4]1[OH:21].CO[C:24](OC)([CH3:26])[CH3:25].CCN(CC)CC>CC(C)=O.CS(O)(=O)=O>[I:15][C:14]1[C:9]([NH:8][C@H:6]2[C@@H:5]3[O:20][C:24]([CH3:26])([CH3:25])[O:21][C@@H:4]3[C@@H:3]([CH2:2][OH:1])[CH2:7]2)=[N:10][C:11]([S:18][CH3:19])=[N:12][C:13]=1[O:16][CH3:17]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 64952,2-DimethoxypropaneHCID 8471TriethylamineHCID 117677905(1S,2R,3R,5R)-3-(Hydroxymethyl)-5-(5-iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)cyclopentane-1,2-diol

Produkt 1

HCID 117677839((3aR,4R,6R,6aS)-6-(5-Iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6395
Methanesulfonic Acid
Katalysator
HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Compound 5 (4.00 g, 9.36 mmol) was dissolved in acetone (10 mL) and 2,2-dimethoxypropane (5.75 mL, 46.8 mmol) was added. The solution was cooled to 0° C. and methanesulfonic acid (2 drops) was added. The solution was stirred for 15 min and Et3N (1 mL) was added. The acetone was evaporated and the residue was dissolved in EtOAc, washed with water and brine, dried (MgSO4), filtered and concentrated. The residue was purified via column chromatography on silica gel (EtOAc/hexanes) to give the title compound as a white solid. 1H NMR (CDCl3) δ 6.21 (d, J=8 Hz, 1H), 4.65-4.59 (m, 2H), 4.45-4.44 (m, 1H), 3.94 (s, 3H), 3.89-3.85 (m, 1H), 3.76-3.73 (m, 1H), 2.61-2.55 (m, 1H), 2.52 (s, 3H), 2.40-2.34 (m, 1H), 1.85 (br s, 1H), 1.65-1.57 (m, 2H), 1.49 (s, 3H), 1.28 (s, 3H); LCMS 2.54 min, 468 (M+H).

Aufarbeitung

  1. customThe acetone was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via column chromatography on silica gel (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-29b201806dd549258b9d8e9107ad2337
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09221809B2

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