Indinavir - An Outl...
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Indinavir - An Outline
Indinavir - An Outline
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The synthesis of the piperazine constructing block of indinavir using a extra convergent, environment friendly, and greener strategy that utilized asymmetric catalysis as a substitute of a decision for cialis flavored online the important thing intermediate 4.4.7, is proven in Scheme 12. An Ugi multicomponent response supplied intermediate 4.4.16, which indocin without a doctor prescription isolation was handled with triethylamine to bear elimination of HCl to afford 4.4.17. Cyclization of 4.4.17 to 4.4.18 was accomplished in 60% yield by carefully monitoring the response conditions and the following key asymmetric hydrogenation was accomplished with 7 mol% Rh-BINAP in methanol to give 4.4.19 in quantitative yield and 97% ee.Forty Elimination of the formyl group with 35% aqueous hydrazine gave 4.4.7 in good yield with out racemization. Scheme 12. Synthesis of the piperazine portion (4.4.7) of indinavir (Crixivan). Reagents and conditions: (a) Et3N; (b) t-BuOK; (c) 7 mol% Rh-BINAP, H2 (100 atm), MeOH, forty °C; (d) 35% aqueous hydrazine. The synthesis of the epoxide building block 4.4.23 is shown in Scheme 13.41 Intermediate 4.4.21 was obtained in two chemical steps from cis-1-amino-indanol (4.4.20)forty two after which alkylated with allyl bromide to afford 4.4.22 in a 96:Four ratio. Scheme 13. Greener indinavir strategy: Synthesis of intermediate 4.4.23. Reagents and conditions: (a) Ref. 42; (b) LHMDS, allyl bromide, THF, −15 °C; (c) (i) NCS, NaI, online voveran sr IPAc, aqueous NaHCO3; (ii) NaOMe, THF. Scheme 14. Convergent synthesis of indinavir (Crixivan). Reagents and situations: (a) IPA, liv.52 online 6 N HCl, reflux; (b) 3-picolyl chloride.

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