(1R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carboxylic acid-(2-oxo-cyclohex-3-enyl)-amide

Base Information

• Chemical Name: (1R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carboxylic acid-(2-oxo-cyclohex-3-enyl)-amide
• CAS No.: 287117-69-5
• Molecular Formula: C₁₇H₂₄N₂O₄S
• Molecular Weight: 352.455

Synonyms:(1R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carboxylic acid-(2-oxo-cyclohex-3-enyl)-amide

Chemical Property of (1R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carboxylic acid-(2-oxo-cyclohex-3-enyl)-amide

Chemical Property:

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Technology Process of (1R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carboxylic acid-(2-oxo-cyclohex-3-enyl)-amide

There total 3 articles about (1R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carboxylic acid-(2-oxo-cyclohex-3-enyl)-amide 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: 63.0%

(1S,4R)-[5-(tert-butyl-dimethyl-silyloxy)-2-oxa-3-aza-bicyclo[2,2,2]oct-5-en-3-yl]-(3,3-dioxo-10,10-dimethyl-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (287117-67-3) → (1R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carboxylic acid-(2-oxo-cyclohex-3-enyl)-amide (287117-69-5)

Guidance literature:

With hexacarbonyl molybdenum; water; In acetonitrile; at 80 ℃; for 12h;

DOI:10.1016/S0040-4020(00)00284-2

Reference yield:

(+)-camphorsultam (108448-77-7,124224-04-0) → (1R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carboxylic acid-(2-oxo-cyclohex-3-enyl)-amide (287117-69-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: iPr₂EtN / diethyl ether / 18 h / 0 - 20 °C

1.2: 85 percent / NH₂OH*HCl; aq. K₂CO₃ / 6 h

2.1: 64 percent / Et₄NIO₄ / CH₂Cl₂ / -78 - 20 °C

3.1: 63 percent / Mo(CO)6; H₂O / acetonitrile / 12 h / 80 °C

With hexacarbonyl molybdenum; water; tetraethylammonium metaperiodate; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; acetonitrile; 1.1: Condensation / 1.2: Substitution / 2.1: Oxidation / 3.1: Ring cleavage;

DOI:10.1016/S0040-4020(00)00284-2

Reference yield:

(7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.03,7]decane-4-hydroxamic acid (188845-76-3) → (1R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carboxylic acid-(2-oxo-cyclohex-3-enyl)-amide (287117-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / Et₄NIO₄ / CH₂Cl₂ / -78 - 20 °C

2: 63 percent / Mo(CO)6; H₂O / acetonitrile / 12 h / 80 °C

With hexacarbonyl molybdenum; water; tetraethylammonium metaperiodate; In dichloromethane; acetonitrile; 1: Oxidation / 2: Ring cleavage;

DOI:10.1016/S0040-4020(00)00284-2

upstream raw materials:

(1S,4R)-[5-(tert-butyl-dimethyl-silyloxy)-2-oxa-3-aza-bicyclo[2,2,2]oct-5-en-3-yl]-(3,3-dioxo-10,10-dimethyl-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

(+)-camphorsultam

(7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^3,7]decane-4-hydroxamic acid

Downstream raw materials:

(3aR,6R,7S,7aS)-3-tosyl-3a,4,5,6,7,7a-6-hydroxy-7-bromohexahydrobenzoxazolin-2-one

(3aR,7aS)-3-tosyl-3a,4,5,7a-tetrahydrobenzoxazolin-2-one

C₈H₁₃NO₂

(-)-(1R,4S)-tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate

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