12401 synthesis

9synthesis methods

Product Name:12401
CAS Number:1254102-12-9
Molecular formula:C18H16N4O3
Molecular Weight:336.35

(R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one

948893-91-2
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1254102-12-9
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Yield:1254102-12-9 92%

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran at 20;

Steps:

5 Intermediate 5: (R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-one

A 1.0 M (THF) solution of TBAF (0.443 mL, 0.443 mmol) was added to a stirring solution of Intermediate 1 (200 mg, 0.443 mmol) in THF (4 mL) at rt. The resulting mixture was stirred over night then concentrated. Chromatography (1:3, Hexanes/EtOAc) afforded the title compound (137 mg, 92%) as an off-white solid. ES/MS calcd. for C₁₈H₁₇N₄O₃⁺ 337.1. Found m/z=337.2 (M+H)⁺.

References:

US2011/275622,2011,A1 Location in patent:Paragraph 0284

530084-79-8 Synthesis