Hydrochloric Acid → 3-(2,3,4,6-Tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-4-[2-(4-pivaloyloxyphenyl)ethyl]-1H-pyrazolo[3,4-b]pyridine

HRID 2223959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223959
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:16][N:17]=[C:18]([O:19][C@@H:20]4[O:46][C@H:45]([CH2:47][O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])[C@@H:37]([O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C@H:29]([O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C@H:21]4[O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:11]=23)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:62](Cl)(=[O:67])[C:63]([CH3:66])([CH3:65])[CH3:64].Cl>ClCCl>[C:23]([O:22][C@@H:21]1[C@@H:29]([O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C@H:37]([O:38][C:39](=[O:44])[C:40]([CH3:41])([CH3:42])[CH3:43])[C@@H:45]([CH2:47][O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])[O:46][C@H:20]1[O:19][C:18]1[C:11]2[C:12](=[N:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][C:62](=[O:67])[C:63]([CH3:66])([CH3:65])[CH3:64])=[CH:7][CH:6]=2)[NH:16][N:17]=1)(=[O:28])[C:24]([CH3:25])([CH3:26])[CH3:27]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 67341046HCID 67341046, Verbindung

Produkt 1

HCID 673408983-(2,3,4,6-Tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-4-[2-(4-pivaloyloxyphenyl)ethyl]-1H-pyrazolo[3,4-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(4-hydroxyphenyl)ethyl]-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazolo[3,4-b]pyridine (1.6 g) in dichloromethane (20 mL) were added triethylamine (0.44 mL) and pivaloyl chloride (0.31 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate =2/1−1/1) to give the title compound (1.76 g).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate =2/1−1/1)

Quellen und Nachweise

ORD-Eintrag
ord-5c8970864dfa4705b51459d2e0e1ba32
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375113B2

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