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

Base Information

• Chemical Name: (7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^3,7]decane-4-hydroxamic acid
• CAS No.: 188845-76-3
• Molecular Formula: C₁₁H₁₈N₂O₄S
• Molecular Weight: 274.341
• Mol file: 188845-76-3.mol

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

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

Chemical Property:

• Density: 1.48±0.1 g/cm3(Predicted)

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R,S,S)-Elenor Amination Reagent ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^3,7]decane-4-hydroxamic 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: 85.0%

bis(trichloromethyl) carbonate (32315-10-9) + (+)-camphorsultam (108448-77-7,124224-04-0) → (7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.03,7]decane-4-hydroxamic acid (188845-76-3)

Guidance literature:

bis(trichloromethyl) carbonate; (+)-camphorsultam; With N-ethyl-N,N-diisopropylamine; In diethyl ether; at 0 - 20 ℃; for 18h;

With hydroxylamine hydrochloride; potassium carbonate; for 6h;

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

Reference yield:

(1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl chloride → (7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.03,7]decane-4-hydroxamic acid (188845-76-3)

Guidance literature:

With hydroxylamine hydrochloride; potassium carbonate; In diethyl ether; for 10h; Yield given; Ambient temperature;

DOI:10.1002/hlca.19970800115

Reference yield:

(+)-camphorsultam (108448-77-7,124224-04-0) → (7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.03,7]decane-4-hydroxamic acid (188845-76-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / toluene; paraffin / 2 h / Ambient temperature

2: NH₂OH*HCl, K₂CO₃ / diethyl ether / 10 h / Ambient temperature

With hydroxylamine hydrochloride; sodium hydride; potassium carbonate; In diethyl ether; toluene; paraffin;

DOI:10.1002/hlca.19970800115

upstream raw materials:

bis(trichloromethyl) carbonate

(+)-camphorsultam

Downstream raw materials:

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

Refernces

• 1、 Chapuis, Christian,De Saint Laumer, Jean-Yves,Marty, Maurus. "14. Origin of Diastereoselectivity in the Thermal [4+2] Cycloadditions of Dienophiles Derived from Oppolzer's Sultams: Steric vs. Stereoelectronic Influences". . p. 146 - 172. Retrieved 2007/10/03.