(3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)-oxy-2H-azepin-2-one

Base Information

• Chemical Name: (3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)-oxy-2H-azepin-2-one
• CAS No.: 270902-69-7
• Molecular Formula: C₁₈H₃₀N₂O₅
• Molecular Weight: 354.447

Synonyms:(3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)-oxy-2H-azepin-2-one

Chemical Property of (3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)-oxy-2H-azepin-2-one

Chemical Property:

Purity/Quality:

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Technology Process of (3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)-oxy-2H-azepin-2-one

There total 4 articles about (3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)-oxy-2H-azepin-2-one 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: 99.5%

cyclohexanylcarbonyl chloride (2719-27-9) + (3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-hydroxy-2H-azepin-2-one (270902-68-6) → (3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)-oxy-2H-azepin-2-one (270902-69-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jm010188c

Reference yield:

cyclohexanylcarbonyl chloride (2719-27-9) + (3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-hydroxy-2H-azepin-2-one (270902-68-6) → (3S,6R)-3-(tert-butoxycarbonyl) aminohexahydro-6-(cycohexanecarbonyl)oxy-2H-azepin-2-one + (3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)-oxy-2H-azepin-2-one (270902-69-7)

Guidance literature:

With triethylamine; In dichloromethane;

Reference yield:

(R)-5-hydroxy-L-lysine dihydrochloride hydrate (2219-28-5) → (3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)-oxy-2H-azepin-2-one (270902-69-7)

Guidance literature:

Multi-step reaction with 4 steps

1: chloro-trimethyl-silane / 3 h / 63 °C / Inert atmosphere

2: triethylamine / methanol / 3 h / 50 °C / Inert atmosphere

3: methanol / 1 h / 25 °C / Inert atmosphere

4: dmap / ethyl acetate / 3 h / 50 °C / Inert atmosphere

With dmap; chloro-trimethyl-silane; triethylamine; In methanol; ethyl acetate;

DOI:10.1021/op0341162

upstream raw materials:

cyclohexanylcarbonyl chloride

(3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-hydroxy-2H-azepin-2-one

(R)-5-hydroxy-L-lysine dihydrochloride hydrate

di-tert-butyl dicarbonate

Downstream raw materials:

(3S, 6R)-3-aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one

(2R,3R,4S,5R,6E)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-N-[(3S,6R)-hexahydro-2-oxo-6-(cyclohexylcarbonyl)oxy-2H-azepin-3-yl]non-6-enamide

(2R,3R,4S,5R,6E)-3,5-(methylethylidene)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-N-[(3S,6R)-hexahydro-2-oxo-6-(cyclohexylcarbonyl)oxy-2H-azepin-3-yl]non-6-enamide

(3S,6R)-3-aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one*HCl

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