ChemicalBook CAS DataBase List Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir

Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir synthesis

13synthesis methods

Product Name:Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir
CAS Number:198904-86-8
Molecular formula:C32H42N4O5
Molecular Weight:562.7

98760-08-8 Synthesis

(2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane

98760-08-8
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tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate

198904-85-7
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Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir

198904-86-8
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Yield:198904-86-8 75%

Reaction Conditions:

in isopropyl alcoholHeating / reflux;

Steps:

1
Synthesis of tert-butyl 2-((2S,3S)-3-(tert-butoxyearbonylammo)-2-hydroxy-4-phenylbutyl)-2-(4-(pyndin-2-yl)b enzyl)hydrazinccarboxylate (XV, Y^Ia = Y^Ib = H).; A mixture of tert-butyl (S)-1-((R)-oxian-2-yl)-2-phenylthylcarbamate XIV (1.18 g. 4.48 mmol), XIII, Y^1a = Y^1b = H (1.23 g, 4.11 mmol) and isopropanol (15 mL) was kept at reflux under nitrogen overnight. The solvent was removed in a rotary evaporator and the residue was purified by chromatography on silica (100 g) with 8:2 dichloromethane/ethyl acetate to give product XV, wherein Y^1a = Y^1b = II (1.74 g, 75%).

References:

Concert Pharmaceuticals Inc. EP2003120, 2008, A1 Location in patent:Page/Page column 33-34

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