* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With hydrogenchloride; In tetrahydrofuran; water; at 50.0℃; for 8.0h;
To a 72-L reactor were charged THF (18.1 L, 5.1 vol), IB-MECA acetonide (3.55 kg, 6.45 mol, 1.0 wt/1.0 vol), and IN aqueous HCl (17.8 L, 17.8 mol, 2.76 equiv, 5.0 vol). The resulting pale green stirring slurry was heated at 50 +/- 5 0C for approximately 8 h at which point HPLC analysis showed 1.16% of IB-MECA acetonide remaining wrt IB- MECA (thus meeting the specification <1.5%). The batch was allowed to cool to approximately 40 C and then filtered through an in-line filter via a transfer pump. The emptied reactor and the transfer line were rinsed with THF (600 mL, 0.17 vol). The resulting filtrate was stored in the cold room (2-8 0C) overnight. To a 200-L reactor was added chilled saturated aqueous NaHCO3 (53.6 L, 15 vol, 16 C) through an in-line filter and stirring commenced. The IB-MECA rich filtrate (15 0C) was added over 30 min to the 200-L reactor via a transfer pump equipped with an in-line filter. The resulting white precipitate was stirred overnight to age (there was little temperature fluctuation during the precipitation which occurred at 20 +/- 2 0C, no cooling was applied, and there was a minor amount of foaming. The pH of the slurry was pH 7.5). The batch was filtered using a nylon filter cloth; the emptied reactor and the cake were rinsed with water (5 x 3.4 L, 4.8 vol). The cake was pulled under a flow of N2 (total filtration time was 5.5 h), packaged for further processing, and stored in the cold room. This batch (9.2 kg wet weight) was shown to be 99.5 area % pure with no single impurity >0.20 area % by HPLC.
(2S,3S,4R,5R)-5-(6-[Benzotriazol-1-yl-(3-iodo-phenyl)-methyl]-amino}-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methylamide[ No CAS ]
3,4-bis(tert-butyldimethylsilyloxy)-5-(6-(3-iodobenzylamino)-9H-purin-9-yl)-N-methyl-tetrahydrofuran 2-carboxamide[ No CAS ]
[ 152918-18-8 ]
Yield
Reaction Conditions
Operation in experiment
95.45%
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20.0℃; for 1.0h;Inert atmosphere;
The intermediate compound (65 mg, 0.08 mmol) prepared in Step 6Then dissolved in anhydrous THF under nitrogen gas stream tert-butyl ammonium fluoride (TBAF)(0.44 mL, 0.43 mmol, (1 M THF solution)) to It was added dropwise and then stirred at room temperature for 1 hour.The residue was concentrated under reduced pressure and the reaction solution after confirming the completion of the reactionColumn intermediate compound by chromatographic separation with (2S, 5R) -3,4- dihydroxy-5- (6- (3-iodo-benzyl-amino) -9H- purin-9-yl) -N- methyl-tetrahydro- furan-2-carboxamide (52 mg, 95.45%) a Obtained.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
