(3S)-9-[9-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl]-3-(2-methoxypyrimidin-5-yl)-5-oxononanoic acid

Base Information

• Chemical Name: (3S)-9-[9-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl]-3-(2-methoxypyrimidin-5-yl)-5-oxononanoic acid
• CAS No.: 758686-10-1
• Molecular Formula: C₂₈H₃₈N₄O₆
• Molecular Weight: 526.633

Synonyms:(3S)-9-[9-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl]-3-(2-methoxypyrimidin-5-yl)-5-oxononanoic acid

Chemical Property of (3S)-9-[9-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl]-3-(2-methoxypyrimidin-5-yl)-5-oxononanoic acid

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Technology Process of (3S)-9-[9-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl]-3-(2-methoxypyrimidin-5-yl)-5-oxononanoic acid

There total 1 articles about (3S)-9-[9-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl]-3-(2-methoxypyrimidin-5-yl)-5-oxononanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

6-chloropyridin-2-amine (45644-21-1) → (3S)-9-[9-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl]-3-(2-methoxypyrimidin-5-yl)-5-oxononanoic acid (758686-10-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 91 percent / hexyllithium; 1,1,1,3,3,3-hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C

2.1: 78 percent / hexyllithium; N,N,N',N'-tetramethylethylenediamine / hexane; tetrahydrofuran / 9 h / Heating

3.1: potassium carbonate; bis(diphenylphosphino)ferrocene / Pd(OAc)2 / tetrahydrofuran / 26 h / 65 °C

4.1: hydrochloric acid / isopropyl acetate / 4 h / 0 °C

5.1: KHMDS / toluene; tetrahydrofuran / -78 - 0 °C

5.2: 53 percent / tetrahydrofuran / 3 h / 0 °C

6.1: H₂ / Pd/C / propan-2-ol; H₂O / 2 h / 2100.17 Torr

7.1: 3.45 kg / NaOH / propan-2-ol; H₂O / 2.5 h / 0 °C

With hydrogenchloride; sodium hydroxide; 1,1'-bis(diphenylphosphino)ferrocene; N,N,N,N,-tetramethylethylenediamine; hydrogen; n-hexyllithium; potassium hexamethylsilazane; potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; hexane; Isopropyl acetate; water; isopropyl alcohol; toluene; 3.1: Suzuki coupling / 5.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo048082n

upstream raw materials:

6-chloropyridin-2-amine

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