(S)-N-[[((R)-1-acetyl-1,2,3,4-tetrahydroquinolin-4-yl)amino](4-tolyl)oxido-λ⁴-sulfanylidene]tosylamide

Base Information

• Chemical Name: (S)-N-[[((R)-1-acetyl-1,2,3,4-tetrahydroquinolin-4-yl)amino](4-tolyl)oxido-λ⁴-sulfanylidene]tosylamide
• CAS No.: 908013-58-1
• Molecular Formula: C₂₅H₂₇N₃O₄S₂
• Molecular Weight: 497.639

Synonyms:(S)-N-[[((R)-1-acetyl-1,2,3,4-tetrahydroquinolin-4-yl)amino](4-tolyl)oxido-λ⁴-sulfanylidene]tosylamide

Chemical Property of (S)-N-[[((R)-1-acetyl-1,2,3,4-tetrahydroquinolin-4-yl)amino](4-tolyl)oxido-λ⁴-sulfanylidene]tosylamide

Chemical Property:

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Technology Process of (S)-N-[[((R)-1-acetyl-1,2,3,4-tetrahydroquinolin-4-yl)amino](4-tolyl)oxido-λ⁴-sulfanylidene]tosylamide

There total 5 articles about (S)-N-[[((R)-1-acetyl-1,2,3,4-tetrahydroquinolin-4-yl)amino](4-tolyl)oxido-λ⁴-sulfanylidene]tosylamide 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: 91.0%

N-[(1S)-amino(4-tolyl)oxido-λ4-sulfanylidene]tosylamide (816444-61-8) + 1-acetyl-1,2,3,4-tetrahydroquinoline (4169-19-1) → (S)-N-[[((R)-1-acetyl-1,2,3,4-tetrahydroquinolin-4-yl)amino](4-tolyl)oxido-λ4-sulfanylidene]tosylamide (908013-58-1)

Guidance literature:

With 4 A molecular sieve; (S)-N-1,8-naphthoylalanine dirhodium complex; In methanol; 1,1,2,2-tetrachloroethane; at -35 ℃; for 72h;

DOI:10.1021/ja076519d

Reference yield:

sodium 4-methylbenzenesulfinate (824-79-3) → (S)-N-[[((R)-1-acetyl-1,2,3,4-tetrahydroquinolin-4-yl)amino](4-tolyl)oxido-λ4-sulfanylidene]tosylamide (908013-58-1)

Guidance literature:

Multi-step reaction with 5 steps

1: thionyl chloride / toluene / 16 h / 20 °C / Inert atmosphere

2: toluene / 4 h / 80 °C

3: sodium hydrogencarbonate / dichloromethane; water / 16 h / 0 - 20 °C

4: trifluorormethanesulfonic acid / dichloromethane / 1 h / 20 °C

5: dirhodium tetrakis{(2S)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid}; bis(tertbutylcarbonyloxy)iodobenzene / methanol; 1,2-dichloro-ethane / 72 h / -35 °C / Molecular sieve

With thionyl chloride; trifluorormethanesulfonic acid; dirhodium tetrakis{(2S)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid}; bis(tertbutylcarbonyloxy)iodobenzene; sodium hydrogencarbonate; In methanol; dichloromethane; water; 1,2-dichloro-ethane; toluene;

DOI:10.1055/s-0033-1339280

Reference yield:

4-methylbenzenesulfinyl chloride (10439-23-3) → (S)-N-[[((R)-1-acetyl-1,2,3,4-tetrahydroquinolin-4-yl)amino](4-tolyl)oxido-λ4-sulfanylidene]tosylamide (908013-58-1)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene / 4 h / 80 °C

2: sodium hydrogencarbonate / dichloromethane; water / 16 h / 0 - 20 °C

3: trifluorormethanesulfonic acid / dichloromethane / 1 h / 20 °C

4: dirhodium tetrakis{(2S)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid}; bis(tertbutylcarbonyloxy)iodobenzene / methanol; 1,2-dichloro-ethane / 72 h / -35 °C / Molecular sieve

With trifluorormethanesulfonic acid; dirhodium tetrakis{(2S)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid}; bis(tertbutylcarbonyloxy)iodobenzene; sodium hydrogencarbonate; In methanol; dichloromethane; water; 1,2-dichloro-ethane; toluene;

DOI:10.1055/s-0033-1339280

upstream raw materials:

N-[(1S)-amino(4-tolyl)oxido-λ⁴-sulfanylidene]tosylamide

1-acetyl-1,2,3,4-tetrahydroquinoline

sodium 4-methylbenzenesulfinate

4-methylbenzenesulfinyl chloride

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